Then, we got the Woke, Bleeding Heart Judges and with a letter of hardship at Mediation the Deadbeat, Single Mother with kids and Older ones on Fixed Incomes could get another 90 days to stay for free.

Lucy,It does look like you are referring to the minimum interest, or prepayment penalty, of your existing lender as well as the 'seasoning' period of any potential new lender.Most HMLs won't have a prepayment penalty on a rehab-bridge loan, but a lot of long term refinance lenders would require a period of time after you purchase it before they would take the new 'after repair value' (or, seasoning).

One cannot compare a forum site with a seasoned investor who answers questions and teaches.

Be a Financial Partner with a seasoned investor that knows the market and be involved to get to know the how to's.Reach out to me if you want to talk more. 

Great thing about Bigger Pockets is you can network and find in any state a great property, seasoned agent, Banker for financing, Wholesaler, GC, handyman/property maintenance to make it all happen.

It depends on the market, size of pool, type of pool (liner, gunite, fiberglass), insurance at your location, availability of qualified pool techs in your market, indoor or outdoor (seasonality or year round), heated or non-heated to just name a few. 

Odds are there is much more hidden here than is being shared.A seasoned investor could probably mitigate these risks, but they would run EVERYTHING to ground. 

To my seasoned investors, what makes the most sense in the area/market?

Will it put you into the slow start of school season? 

However, the jurisdictions continue to apply rent control to older units when an ADU is added.