The funny thing about insurance is the more you need it, the harder it is to get. As soon as you have a problem - points on your driving licence, a health condition - you become high-risk and the financial outlay goes up. In extreme cases, it may prove difficult to buy any cover at all.

These questions have been preoccupying me since I developed a rare autoimmune disease, undiagnosed for months but now happily being treated. In fact, I have two autoimmune conditions, an overactive thyroid and a condition called pemphigoid, which, as Oscar Wilde might have remarked, looks rather like carelessness.

The financial fallout from these conditions underlines my point. As a freelance, I found the illness - and attendant uncertainty pre-diagnosis - not only slashed my ability to earn, but also underlined my short-sightedness in not insuring myself against this eventuality. Even worse, I have no health insurance to speak of and now may find it tricky getting any.

Researching what I should have done in an ideal world, I asked insurers three key questions. Would they give me health insurance now, with my autoimmune conditions? Would I have been able to secure my freelance earning position pre-illness? And what are my chances now?

I began with Bupa, as its leaflet had fallen out of a Sunday paper. Bupa is the grandaddy of health insurers, 'older than the NHS' as the helpful phone broker put it. Founded in 1947, it is now this country's biggest health insurer.

I was impressed by the 10 per cent discount Bupa offers the self-employed. We discussed my rare disease, mucus membrane pemphigoid, the woman consulted her health expert, and came back with the expected answer. No cover for the two autoimmune conditions, or any related health problem.

But I could get cover for everything else - including paid-for consultation if it turned out a health issue wasn't related to my autoimmune status. Cost: just over £60 a month for full-ish cover: consultation at private hospital, private room option, medical tests and operations. Oddly, apart from the autoimmune stuff, I'm a reasonable risk now, having never smoked and now being unable to drink.

The Heartbeat Select 2 option also has a cheaper sibling, costing £46.14 a month, which excludes consultants' fees but includes diagnostic tests and in-patient care.

Norwich Union also caters for freelances. They didn't like the sound of my illnesses either - who does? - but offered their Trust Care Starter policy covering in-patient care only at a reasonable £59.65 a month. Obviously, existing ailments would be excluded.

I moved on to the income protection I should have taken out. If I had gone ahead a year ago with Norwich Union, protecting a nominal £15,000 a year (enough to cover our mortgage and key bills) would have cost me, at age 48, £50.45 a month. This could have provided a handy £750-a-month income replacement -starting after 13 weeks' illness - until age 60. Frankly, this would have been a good deal.

And then there's Saga, so sussed it knows the magic 50th birthday of every British citizen and markets to them accordingly. I'm about to hit the crucial age, so asked for its best deals. Known to be good for mature drivers, Saga offers health insurance, too, but no income protection as its core clients are mainly thinking about retirement.

Saga's Super Cover has no limit on in-patient treat ment. All out-patient consultations and tests are also covered. You also get home nursing, recuperative care (yes, please) and alternative treatments, including osteopathy and acupuncture. This would cost from £88.26 a month or an annual premium of £979.64 for a 50-year-old choosing from Saga's countrywide hospital list. A London hospital upgrade is available for about £13 a month extra. Paying a £500 excess rather than £100 would cut the bill by 20 per cent.

I also consulted my own bank, NatWest, which provides health cover via Norwich Union. But I'd gain a 10 per cent reduction as an Advantage Gold current account holder.

Kent-based Independent Insurance Brokers offered good income protection advice. For just £35 a month, I could protect my notional £15,000 survival salary, excluding payouts for illness related to my diagnosis. Monthly payouts of £800 would start after 30 days, providing the terms of the insurance were satisfied. The company's Ray Johnson pointed out: 'You have to be careful you meet the requirements. It's easy with straightforward diseases such as heart disorders, but you would have to prove incapacity.'

So how do you get a good, tailor-made deal?

· Shop around, as with anything else;

· Don't overstretch your resources;

· Look out for good introductory offers on the internet or via your bank;

· Don't accept the first policy offered - it may be a new policy they are trying to hit targets on;

· Try the smaller independent insurance brokers: they can give you information on smaller, specialist insurers.

My own solution looks like healthcare from Bupa and income protection from a Folkestone independent broker. The one thing I shan't do is leave insurance until tomorrow - I've learnt my lesson but good.

· Bupa 0800 600 500;

· Norwich Union 01603 6222200;

· Saga health insurance 0800 857857

· Independent Insurance Brokers, Folkestone 01303 221188