.: Stessa isn't good for keeping track of tax deduction items.Stessa was designed to just look at P&L.

Another downside is you loose on the advantages, of the Federal Tax Code, by not closing in the name of a LLC (you can elect to have a LLC taxed, as a S Corporation which is a whole other conversation).If you want to close in the name of a LLC, Mortgage Lenders will offer you Commercial Loan Terms (25-30% down, a 15-25 year amortization, and a ballon due in 5-7 years).

You mentioned gross rents of $3400 per month and Principle/Interest/Tax/Insurance of $2500 per month. 

The revenue and expense categories line up with your Schedule E which makes it a breeze to prepare for filing your taxes and I like the reporting features, too.

After collecting tenant pass-throughs for the year, do you pay the property taxes at the end of the year or the beginning of the next year?

Assuming property taxes + insurance added don't go above $1,100 total, you could maybe make this work. 

House needs some Interior Cosmetic Work, Wood Fence Repairs and some Plumbing Work.I want to turn and run, but I recently heard where there is a Problem, there is Opportunity.I thought this might be an interesting Case Study.Thanks for the Ideas.If they owe $180k on a $210k property and its a year+ behind then they probably owe taxes and other bills as well.

The 1031 exchange will indefinitely defer all tax on profit and all depreciation recapture.

Great hosts will be good neighbors, will contribute to local tourism and will pay their taxes and permit fees* A major area to improve on the proposal is the 1 hour time-limit for resolving complaints.

My tax professional is stating that I would need an appraisal to show the lot/structure are valued at $400k if I try to claim $200k as a donation.