I have a similar situation that I was hoping to get some advice on.

The situation is very fact-specific, but if you're looking at the rental property on a risk-reward continuum, do you really want to take the risk of owing a tenant a boatload of money at the end of the lease term?

I’m currently in the same situation.

This means we essentially lose a month's rent (August) by the time that they inspect, make their offer and approve the deal (if they do at all).This is obviously a big disincentive for us as landlords and a bad situation for voucher holders as well.I was wondering how others are handling this gap?

Some of the Substantial services : Cleaning of the rental portion of a property while occupied Concierge services Guest tours and outingsMeals and entertainment Transportation Other hotel-like servicesI am not familiar with your situation, but make sure you are not paying SE taxes when you dont need too. 

Following because I'm in the same situation (want to refi or get HELOC on my 3 fam, but looking to invest in another close market)...

You tell them that you buy homes in just about any condition/situation and you can close quickly.

I may be in this situation very soon.

I don't have advice for your personal situation but I will share that I've faced the same challenge. 

When I think about this living situation, I view it as more of a "college living" situation, I guess my perception is hindering me.