The reason you have several potential approaches is because we are all starting without all of the info.  

So far I would say it has been a good investment but I don't really know how big I can scale it or how long it will take.At the same time, if there's a big investor looking for someone to help manage their portfolio in NYC or Long Island I would be open to jump on board so I can learn as well.

I will check into those companies you suggested and see what they have to offer and if it will fit what we are looking for. 

Hey fellow investers we are a investing couple that is still pretty new to this.

We are considering using the rent to own strategy with our newest deal, a 2 bed, 1 bath.

With that being said if you're using an esig software we are talking about a few clicks why not just do it the long way to be safe. 

My loan officer agreed that providing a lease agreement before closing will help, but I also need to provide a solid reason for why we are downsizing to this extent.What reasons can I give for making such a significant downsize?

If you are getting a HomeReady mortgage (for Fannie), then you can count boarder income as long as the boarder has been living with you and paying rent directly to you for a year.

Then if you want to pick up a first time investor buyer and show them the ropes of the most successful long term investors in your market you can share your time and expertise now and then.

The reality that neither view is realistic or probable.The best advice I can give would be to underwrite for long-term leases as that can be an acceptable exit strategy, but be prepared to execute well on your MTR strategy (great interior design along with profesisonal photos and concierge servive).