In my opinion, it would be very difficult to manage long distance with no boots on the ground.

Condos often come with an HOA on top of the property tax as a fixed expense that you'd have to carry in the event of a non-paying, difficult to evict tenant. 

Hey Brandon,Unfortunately getting loans from banks and PMLs is difficult when you don't have an income.

@Julia Kulbatzki while it is difficult to point to one that consistently outstanding, there are a few that seem to do quite well overall.

They can go very bad, or very good, and it is a very difficult line to walk" 

Bought a house in Brantford before the market exploded and want to BRRRR a property, but it seems extremely difficult to do given the cost of houses here.

BRRR is difficult here as prices are being pushed higher with low inventory.

I feel like condos are the way to go but I'm not sure about the exit strategy: will the condo board allow renting after I move out, how difficult is it to deal with a tenant in a relatively landlord-unfriendly market like DC, etc.

ARV is a little difficult as this property has nearly no near identical "comps".

Late fall through January is a really difficult time to find tenants so it's nothing you are doing wrong.