This is a physical asset, not paper, and it's providing consistent income.Albeit for your not understanding tax laws and depreciation, I'm wondering why there's a question as to what you should keep.You understand capital gains, but I'm pretty sure you're not familiar with depreciation and loan paydown.

Contrary to most business lending, the REI industry has a lot of "non-bank" lenders that provide attractive loans that can lower your cost of capital and improve your profit/cash flow. 

The idea would involve working together to construct a road that provides access to my property.From there, I’m considering developing a 16-unit multifamily project on my land.

B2B Bank had just introduced liquidity requirements which seemed to indicate they really did not want to be providing that service.TD was the last of the Big Five to offer the ability to write and hold arm's length mortgages.  

Of those two, I actually like the first one better because you have a competitive advantage to that market and the amenities you could provide.

If you sell your only overachiever to go with a more leveraged position, you could have 2-3 properties that may cover themselves or even provide a little profit, but when the rental markets shift (and they do), now you have 2-3 properties that all require you to supplement for their shortages. 

House hacking will provide you with an onramp, though, and make it much easier to get started. 

So that the tenant rent is providing a larger amount of return of capital. 

In your case, transferring the property from a revocable trust to an LLC where you and your wife are the owners should not affect the 1031 exchange, provided the LLC is a disregarded entity for tax purposes . 

Right now, I’m focusing on investing in Providence, Pittsburg, and Allentown.