I wrote an entire post on how to file your tax returns that so that they are more friendly to lenders you can read HERE. 

I'm Jarrod from Ohio, passionate about real estate investing for many years but only now getting back into it after 2 decades.

After a certain number of days vacant, coverage lowers for certain perils.  

In theory after you have made timely payments on their loan that should be considered, but in practice I have yet to find a loan a officer that can package it so their underwriters will except it. 

After you review these numbers you will be able to see if your goals are in line with what the market will deliver. 

What are the book keeping and occupancy tax challenges that are faced?

or just filed tax returns capital gains for the average? 

With the current interest rates, it is a lot less work than a rental and she'd probably make about the same (if not more factoring in property taxes, insurance and repairs). 

Beside the “subject to” that’s recently become the subject of much debate we utilized  ”no interest short term owner financing”, the “2nd mortgage crank”, substitution of collateral, mortgage subordination, wrap loans, real estate “exchange” (not for tax reasons), sale - lease back, guaranteed rent payments, sale - buy back, land offered in lieu of down payment, zero coupon bonds as substitution of collateral, and a few others that escape my memory.  

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