@Kristian Conway I do think that students prefer SFHs over MFH so yes to answer your question.

100% preference.

Your worst-case scenario (not specific to MA) would be having to sue to get them out as a holdover, but this is really reserved for worst-choice scenarios when owners choose the first renter or don't do any due diligence.

Also one with low fees, and preferably not cloud based or revenue share based, any recommendations are greatly appreciated, thank you!

Most prefer havng the entire space to themselves and they don't want to pay a lot.

Due to personal faith based reason, I prefer to only invest in all cash deals that don't involve traditional financing (so typical passive RE options like syndications, RE funds with fixed returns, REITs etc are not a viable option for me).

I figure my options are to sell and take a loss (not ideal), or preferably find coverage that allows or doesn't care about the K&T.

Prefer light renovations/updates, and ability to force equity with opportunity to add ADU(s). 

Using the 1031 Exchange is THE way to defer capital gains taxes and use your equity to purchase additional properties.re: the Pittsburgh market...it can be a good choice.

I would prefer not to keep all my eggs in one basket.