Sounds like trying to force a square peg in a round hole.Just get a round peg.

Can you find a place within the area that has year-round pull...?

It is one thing to have a good realtor, but a well rounded understanding of the neighborhoods, streets, and points of interest to potential renters is key to making sure you have a desirable property. 

We are just entering Phase 2 - depending on this round's financing, we'll do Phase 2 fast or slow.

Obviously $20k is not an estimate, just a round number for the example :). 

It already sounds like you want it too much and are trying to fit a square peg in a round hole.

Start with round #'s and work to continuously sharpen them as you check-off due diligence items during your feasibility process. 

Round up your totals and plug 'em in.

Learning all the roles can make you well-rounded, but it sure will slow you down (if scaling is the goal).Also, read "Free to Focus" by Michael Hyatt to answer this question but in the words of the book: If you don't enjoy it and you aren't good at it, you shouldn't be doing it. :)

So he jumps right into it and its wrong, third go round its still wrong but he's there everyday working through it and fixing his mistakes on his dime.