This is a question that only you can answer, Manny, but we can certainly give you advice.
I bought my first Ferrari this year (a $130k 550 Maranello), and I am also a regular working Joe who happened to come into some money. I do not consider myself to be poor, but I do not have 300k in investments like you (yet) and the house is not paid off.
Principally, I reasoned I could give my dream car the green light if the following conditions were met:
1. I should, in principle, not have to borrow money to buy the car. I did borrow a small amount in the end to give myself more breathing room but it was not required.
2. I should be comfortably able to pay for all ownership costs from my regular salary, without giving up house payments, monthly investments, holidays and generally enjoying life.
3. When considering ownership costs, I would take ALL costs into consideration, particularly depreciation. If you buy a car for $150k, you run it for two years @ $10k a year (fuel, tyres etc) and you sell it for $110k (very likely if you buy a 2004 Modena), it will have cost you $60k, or $2,500 a month. And this excludes any misfortune (drive train packing up or something like that)!!!
4. If I could not afford the car I wanted, or if I thought it would look too unattractive, I would buy a cheaper model, using the money saved to keep it running for several years. The hierarchy of desirable Ferraris, for me, was 1) 550 Maranello, 2) F355 Spyder, 3) F355 Berlinetta, 4) 328GTS, 5) 308 GTS.
Anyone of these cars would have made me a happy man, but the 550 was the first choice. So, it was very important to gather as much info as I could regarding the total ownership costs. These forums are great and you can find a lot of info if you look hard enough.
In the end, it transpired that if I took a long-term view on ownership (drive the car to 100.000km on the dial, sell it for 60,000 euro), counted on a major break down every 35,000km, drove 7,500km a year, had the car stored at a Ferrari specialist, I would need to count on between 1,200 and 1,500 euros a month (depending on which car I bought). That amount includes servicing, labour, brake pads, fuel, tyres, insurance, you name it! This is for a car in Holland, mind, which is an expensive country to run them in. I'd say the same car in the States would come to about the same number, but in USD.
I was very comfortable with being able to cover this cost, and so went ahead with the purchase.
5 months into ownership, I can see I've been a little optimistic on trade-in value already, the 550 still dropping in value. However, on other costs I've been underestimating and so I am still very happy I'll be able to keep the car for a long time.
So, I suggest you do a similar exercise for yourself. Find out as much as you can, and then see what you will be comfortable with. Be conservative when you do your estimations, it is much better if the car turns out cheaper than you thought. I like Boxer's suggestion that you should invest half your budget - I should make a plan in that sense as well. I'm very confident my numbers are correct, now that I have spent less I should put some money into a "Ferrari account" for any big bills coming.
I hope this helps! And I hope you make your dream come true. But please remember: the "cheap Ferrari's" are still dream cars, and will make you smile time and time again. My friend has a 308GT4, which I always thought to be a less succesful design, but I must say I love that car. Like any Ferrari, they seem to be living organisms. So if you decide to go the safe option in terms of purchasing cost and depreciation, you are still in for a wonderful experience.
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