I believe the answer is no because there would be different taxpayers on the title but any thoughts?

But, if the cost is fairly nominal, maybe under a couple grand, and you have no experience in real estate, including owning your own home and hiring contractors for that, then it is likely worth it.I would always start with a deep assessment of where you feel you don't have adequate knowledge.  

Property B,  my co-owner lives there full time while I live in property A (he has no affiliation to property A).My question is, how should I view the monthly payment breakdown of property B (further details below)?

But a lot of GCs can't even afford to do that, because they give their subs constant work. 

@Kaden Flores How much work are you prepared to do?

I have been educating myself on real estate and markets for the past year but I have no connections to a potential team. 

I also go to the website (no info - just an e-mail capturing page).  

I always use TurboTax and it works beautifully for me, but should you feel uncomfortable doing it yourself obviously file an extension and look for someone to support you. 

I specifically only work with investors and investment properties.

If there is no real estate agent involve we provide the 2% discount back to our customers or we are happy to pay the buyers broker such fee.