I am a member of the Oxford House community and I've been studying real estate investing so that it only makes sense that I bring these two worlds together and be of service.

I assume based on the price point these are C/D locations at best but if you can point to reasons why these Sub 100K housing communities will transition to better neighborhood and appreciate then perhaps the voucher program makes sense.

I've looked at a few properties and used excel models to input the numbers and do the calculations but ultimately none of them made investment sense.

Robert Cialdini notes that creating a sense of reciprocation is one of the best sales tactics out there, even if the items being reciprocated aren’t anywhere near equal in value (like a 12-month lease versus a $25 gift card, for example).

Make sense about spreading costs out more, and building bigger since you'll always have the costs of the foundation, roof, etc regardless of the size. 

She keeps saying she will allow to paint once we find a tenant, which makes no sense. 

It has to make sense.  

It would be like leaving fireworks for kids in a sense.

I’m unsure if HEL or HELOC or selling the rental, doing 0% balance transfers makes more sense, or a combination.  

Depending on your financial situation, negative cash flow for a couple of years may make sense (talk with your CPA).The local REIA is a great spot to connect with other investors, there is one at Mazama Brewing every month in Orenco Station.