From my experience working with over 400 investors, I’d recommend starting with house hacking—ideally a fourplex if you find a good deal, but a duplex works too.

In December the roof was finally repaired, however the damage to the ceiling has not. 

Quote from @Victor Yang: If I gift a house, what amount will go towards the lifetime gift limit, the amount i purchased the house for, or the current FMV?

If you can get all the bedbug containing furniture out of the place and it will sit for awhile (or let it sit while the other repairs are done) you may be able to avoid some cost, but if you want to get a paying tenant in sooner rather than later you will want to bite the bullet and get it well done.

I’m currently house hacking in a duplex with a 130 yr old fieldstone foundation.

it does allow you to repair things outside of the home to a limit. 

House gets foreclosed on when a borrower is not paying its debt obligations - typically its mortgage.buying foreclosures is not for the faint of heart as you have no idea of the interior of these properties lastly while it can be beneficial also realize if there are a lot in an area those homes are the new comps when trying to sell so it lowers home values in an area 

It was also difficult to assess the heating situation after repairs since tenant refused to provide key to access unit for repairs and/emergencies, citing “privacy and safety” concerns.

View reportI'm looking to pitch this to an investor who wants to flip this house in Nashville, TN.

Repairs will be done this February and both sides will be rented out.