Or wanting to increase rent and loosing a good tenant because of it… Plus, you can’t trust Rentometer  much either.

House Hacking provides significant financial benefits through appreciation, loan paydown, rental income, and tax savings.

As a last resort, I would even be willing to lease the land, provided that I be compensated for the improvements when it sells.TIA

The receipt also likely needs to be provided to the tenant within 30 days of their lease ending.

Your best bet is find a lending broker you trust and like working with and they will almost always have a loan product to help you fund! 

He wants to make a little more on his money than a CD will provide.

I am hoping that a solid boots on the ground person whom I trust will help make the process less daunting from afar. 

I have been the gc for my flips as well and trust me those skills you have are needed! 

Bookkeepers are fairly inexpensive for the value they provide.

Working with a good investor-friendly realtor would be helpful, but always keeping an eye open and looking for alternative lead streams never hurts as well.I hope that helps, but having contractors that you trust and being ready to move when the deal comes up should put you in good shape going into the spring.Good luck!