I am 21 and was accepted into medical school and will start this summer.

Keep looking to educate yourself, but also prepare for price increases by summer. 

I find the lower unit tenant somewhat peculiar, given he is in the lower unit there will be more heating need as it is much colder in the lower unit but he prefers the vents completely closed in winter and interestingly has more cooling needs during summer than the upstairs tenant.

I'm down state in New York, and if I filed right now, I'd be looking at getting an actual court date maybe sometime in the summer, and that's assuming the eviction ban doesn't get extended again. 

It’s also harder to find tenants in January so this will most likely push you to spring or summer when more people are moving and rents are higher.  

The idea is to live in one of the condos and then rent the other and during the summers move to the other.

In 6 months it will be summer and that's usually an easier time (here anyways) to find a new tenant. 

Our mountain community has many unique properties - this property used to be a small summer resort consisting of 5 small cabins that had been in one family for about 70 years.

Account Closed I just did a few cash out refinances on rentals this past summer in Richmond.

I then gut renovated my apartment this summer and the leak just came back (not long after another storm, though not sure exactly when as the apartment is currently empty.I had a plumber out who said it might be piping or the exterior and I had a general contractor out who said it was very likely the exterior and the whole building needed to be sealed.