We're actually looking in Hagerstown, MD; Erie and Pittsburgh, PA.

If not, you will have a steep burden to prove you were able to actually fulfill your end of the contract and have a court order the completion of a sale. 

I was actually just thinking about this the other day.

I was actually supposed to have a call with Brian today to discuss their second fund and he was a no show.  

I'd like to take a deeper dive into subject to, wraps and other related things to educate myself and see whether some of these might be things I can actually utilize in my real estate journey. 

We've actually previously had two potential buyers come forth, one w/ $20k & one w/ $30k - unsolicited offers that we let get away before we even considered owner financing (or knew what it entailed).

You could also get a line of credit for about $150k (you should be able to borrow 75% of the value.)The reason I suggest this is…1) you save $40-$60k in selling costs. 2) you have a lower blended interest rate (2/3rds at 3.25% and 1/3rd at 7 or 8% instead of the whole $500k at 7 or 8%) saving you another $1k/mo in interest. 3) you only pay interest on that $150k when you actually use it, not from day 1  Unless you hate this property, or want to buy something you can’t afford without selling, that would be my plan.

I'm going to reiterate what's already been mentioned above, but I'm going to actually give you examples of why it's relevant to you to find a U.S. tax professional.1 - You're going to need to file U.S. taxes once you have property down here, there's federal filings, state filings, and sometimes local filings too2 - Tons of tax treaties between the U.S. and Canada that are easy to miss and can cost you a lot of money (important one with rentals - effectively connected income - if the professional you talk to doesn't know what this is, run away)3 - The amount of days you spend in the U.S. needs to be tracked and if you go over a threshold, all of your worldwide income could be taxable by the U.S.4 - Selling real property means up to 15% of your sales proceeds might not be available to you for years (FIRPTA)5 - Lots of nuance at the state and local levels, which both want to take as much money from you as possibleMain takeaway here is that you should find a U.S. based tax person.

Either way, $600 in cash flow should actually help your personal DTI if you go for conventional financing on a primary again. 

I can tell you what we actually did.