Kirk Ellis wrote ...
....if all you had was 50k and what criteria would you apply
to base that decision?

You did a good job of defining your mission (short notice pleasure flights,
one or two long x-counrty trips a year where you'll park the plane for a few
days, mostly two souls on board, sometimes with room for baggage or another
pax). I'd say this is the mission definition for 95% of all recreational
pilots.

This can be met by almost any 4 seater (150-180hp), fixed pitch, fixed gear.
Your "low time" will not scare any insurance co, and your operating costs
will be managable.

Beware of "ego driven mission creep", where a little voice says you really
need a turbo to get above the weather or a gas sucking heavy hauler for that
"imaginary once in a lifetime" trip to Oshkosh with all your hanger buddies
on board.

If you are flexible on plane brand, a craft for your mission can easily be
had within an hour's flight of your homebase (northern FL?). Start telling
everyone, especially A&Ps, that your beginning your search. The number of
planes seen by IAs at annual with under 20 hours is now the norm, and most
of those owners are thinking about selling.

Remember also that the real money issue is seldom the buy-in. A $40k cash
offer with additional ($1k for pre-buy inpection and title search, $2k
insurance, $4-6k first year maint/annual) will keep you in your $50k range.
But you need to look at your "cash flow" as well. I think this is the more
important issue for most pilots and determines if the owning experience is a
happy one, or not.

Most pilots I know experience anywhere from $2k to $12k per year average
flying expenses. For most of us recreational flyers who don't shelter the
plane in a business, this comes as after tax money (expense). Figure out
what yours has been for the last 5 or 6 years. If you were renting and you
have about 150 hrs since 1998, then I'm guessing your cash flow was about
$2k-3k per year at most. Get ready for minimum out flows of $5-7k per person
per year in a partnership of two. This is at the minimum end of the cost
range, assumes you'll each fly about 50hrs per year and have no major
breakdowns or decide to do a $20k interior and paint job (see how expensive
ego can be?)

....Besides, at 55 I really don't want to have to wait a year
for my financing to work out....

Oh,...you don't have enough disposable ($25k) right now for your half of the
partnership? That is a warning sign (not a stop sign, but certainly time to
rerun the checklist).

By that time I will be just a couple of years shy of 60 and
who knows how much time will be left for flying.

You are doing the right things now to give yourself a better shot at a
"happy ownership experience". Don't go "all in" or get upside down. It's
your first plane and you can't get out as fast as you think. Looks to me to
me like you are heading in the right direction. Good hunting and good luck.

PS, do a google search in r.a.o. for a post I did a few weeks back with a
subject title:
snapshot of SEL market
It shows, IMHO, the impact on resale value of one plane over the last year.
It's a buyers market out there.