If you could go in person that helps. 

Becoming a landlord is more work than the average person thinks.

House hacking will also give you some personal "property management" experience.

LLCs offer no tax benefits, they mitigate liability and the fact that this is on your personal property and you'd be renting to yourself, there's no liability to mitigate.

It has not been well maintained over the last 19 years with a string of just bad renters and the person I had managing it just didn't do good quality repairs or work to it. 

This has been the case for me personally.

This clock is ticking Novermber is the last chance that I could save tax on capital gainsAny experts here, please share your thoughts on this situation.Assuming you want to stay in the game, what are your long term goals? 

I would prefer to manage everything through the LLC's account for bookkeeping and tax purposes.Proposed Solution:Open a new joint personal account specifically for making mortgage payments.Transfer the monthly mortgage payment amount from the LLC's business checking account to the joint personal account.Document these transfers as "Owner's Draw" or "Owner's Distribution" in our accounting records.Use the joint personal account to make the mortgage payments.Questions:For the CPAs and accountants out there:What are the tax implications of this approach?

Everyone is going to give you their own "personal" preference.

They will allow your mortgage payment and any personal debt payments (credit cards, cars, etc) to reach about 45% of your monthly income.Programs vary all over the place so it's best to ask a mortgage broker which programs you qualify for.They like two years on the job, rent paid on time, no liens or judgments, pay stubs, tax returns and so on.FHA has a 3.5% down program plus closing costs.