get references, check work (in-progress, if possible - good contractors keep the site clean - even if you can’t tell an EMT from type L pipe, you can tell if the site is clean).
the ‘detached garage with apt above’ is, in fact, a second residence - CHECK ZONING!!!
If you put in a pool, expect to live there the rest of your lives - they do VERY little to improve the selling price of the home.
If the work is to be done in phases, work from the back of the lot forward - don’t put the second house down and THEN realize you’ll need to get a mixer truck in to pour the pool.
Also, you may run into problems with water, electrical, and sewage capacity - find out FIRST if adding another kitchen/bath(s) will exceed the sewage capacity - and if you’re going to heat that pool electrically…
and another big GOTCHA that may be waiting - the 2[sup]ND[/sup] story addition - if the external walls are not strong enough, you will not believe the cost - if your house was built since 1950, you should be OK - check the external wall studs - they should be at least 2x6 on 16" centers (my house uses 2x4 on 16" - CUTE).
Also, your current ceiling beams were designed to hold up the plaster/gypsumboard ceiling. They will most certainly NOT be adequate as floor joists.
See if there is a contractor familiar with such work on such houses in your neighborhood - he/she may be able to supply the engineering required to get the permits - otherwise look for an architect.
Notes:
the above assume frame construction on min. 8"x16" poured concrete footing.
if septic tank is used, good luck - I have no idea how to test for available capacity