I like quicker type transactions to keep the ball rolling but these issues arise all the time.

I feel that just analyzing deals is a great way to feel good when the opportunity arises.

The question then arises when should you segregate?

I am a complete newbie but have a rising interest in REI.

This growth has led to increased property prices and a rising number of people moving to the city for job opportunities.

Not to mention, with a rental property, your liquidity will be zero to none and when a problem arises, that $40,000 will have already been utilized as a downpayment on your property. 

Zoning bills are frequently passed to promote new housing and development but there are plenty of neighborhoods in Philadelphia that have seen a rise in demand where the the zoning is more restrictive. 

Honestly, I doubt it will come up with him, but could arise in legal review.    

If you constantly refinance out your equity in a rising market, and then use that equity to reinvest in the same market, it is not too dissimilar to selling your properties, taking the cash, and then rebuying into the market at the current market rate.

Why don't you use a trsut instead, the trust can be done for estate planning issues which will keep things as they are, there are no due on sale issues with transfers arising from estate planning.