Even before the covid moratorium, they could live there for up to a year without paying anything until the city finally sends the Marshall to kick them out, provided you took immediate proper legal action (and they know how to play the game).

It sounds like you have other issues at play. 

Maybe play dumb a little "I don't know if I'm in the right place..."

FYI will be less cash-intensive (i.e., less money down) to buy a single-unit property and have roommates pay you rent than to buy a multi-unit property. 

These questions all play into my personal decision on whether to hold or sell a profitable investment property. 

You need to play hardball if you really want this property vacant.

The bigger issue for me is the home is almost 100 years old and it isn't in the best of areas for 95k and its definitely not an appreciation play.. but based on ROI I think its still a strong move for the LT hold.. any advice is appreciated!

Hey @Luke Trovinger,Appreciate the response, I will definitely take a look at those and play around with them to see what may work for my market.And good to know for the closing/holding costs, i will try to make some calls around my market find more info on that!

If the initial capital outlay is too intensive for you, you could also negotiate and lease with the option to purchase.

Hi, Yap....roofers are the ones that typically deal with installing skylights.Pay close attention to where the leak is coming from, is it from the Skylight itself or the housing (and thus flushing comes into play) that the skylight sits on?