Alternatively, I was considering bridging the two units and converting it to a luxury family residence (neighborhood does hit million dollar homes) but not sure if the market will support the price tag (this part is easier, and I think the fact that the current owner who claims to be an investor himself yet hasn't made it work... this tells me it probably isn't favorable towards a flip). it definitely is not favorable as a duplex rental so the only way i see it working is to add doors.

I tried following up with him more regularly but he didn't get the hint.

They will recognize your default is “no” and that when you come to them with a “yes,” it is a strong opportunity.A while back, I was on a long run with a friend, Weston, whom I regularly trained with.

I actually confronted the realtor after the sell and she claims it was an cash offer but still 50k is a lot to pass up.

for "regular" residential investments, the maintaining the limited liability aspects can actually confound and/or make it prohibitively expensive for a single investor to do. 

This provides a method to cover the injured student without it going to a Lawsuit/Claim. 

@Mason JeffriesYes, sounds like your issue is because you are renting out rooms, as opposed ot a whole unit...As mentioned, for a "regular" rental, lenders will take your SchE portion of your return, back out the depreciation being a non-cash deduction), take 75% of the rents, then re-calc your profit/loss. 

GOSSSHHHHIssues:• 25k over rehab budget• 3 months over estimated timeline• Someone stole all the flooring• Had to submit an insurance claim• Windows took 6 months to be delivered• Had to evict a tenant• Cash to close on the HUD was higher than expected • Had to extend the hard money (short term) loanReal estate is fun but it’s not easy.

A tree fell on one of my properties, and the other party is denying my claim. 

That fit is too much work for a regular house hacker who does not have a reno loan and it can't be lived in as-is and not enough meat on the bone for a flip for a full-time investor or contractor.