We bought it as a 4 unit and he converted it to a legal 5 unit after closing which made the cashflow substantially better.

It seems like you're headed in the right direction. 

Gary purchased a flip at a substantial discount and finished the rehab.

60 day minimum if you can issue a NTT - not guaranteed  - need to check with attorneyand are tenants way under market or can you go under the guise of "substantial remodel"You have to weigh the upside vs costs and make that calculation.sometimes it might be best to raise rents and wait it outor do a voluntary vacany with the assumption of going to do a remodel and if that is the case go all in and issue everyone the same notice and relocation costs so you are not singling anyone out etc and covers you incase it comes back 

Asking other students if their current landlords are considering selling is a great way to get a head start on the process.

In my job, it's all about getting the right heading/speed and altitude, but when it comes to real state, I don't even know where the runway is!.

But, for future projects, I would be looking for contractors that do not require a substantial amount of payment until the job is 100% done, punch list and all.  

Prop values are about 10x local household income.So on one hand, I'm eager to do my first deal, but on the other hand my gut is saying that market has topped out and is about to head down the roller coaster.

Prices nationally have jumped between September 2020 and September 2021 and have risen around 25%.We now have seen that they've extended the moratorium on foreclosures out from March to June, so we're headed to that September time frame where we think that maybe things might start to free up.

With closing costs, for us to move into this house it will cost 75k, which is a substantial amount of our nest egg, as well as it seems very counter productive from a real estate investor view.