First wholesale deal question.I've got a property under contract with a $100 earnest money deposit.  

If you could find a duplex property (or a single family house that could be turned into a duplex--check any HOA restrictions first), or a "fixer upper" to live in, that could be a better use of the equity you have in the rental house.If you run the numbers and decide it makes sense to sell the rental house (check with your accountant, figure out closing costs to selling and buying) then you'll possibly have more money to put towards a primary residence.You may want to check the neighborhoods that fall in the school district you want to stay in and look in "under appreciated" areas...maybe not the A class neighborhoods, but ones that have potential of becoming "improved".While I understand your desire to stay in a particular school district, it's not the end of the world to consider other districts if they will allow you to build real estate/family wealth that will put your entire family tree in a better position."

By harder, I mean finding deals that actually pencil to even modest positive cash flow returns.  

I've actually talked with multiple STR owners in Hocking Hills, OH (very similar market to Red River Gorge) and they are able to get 90% occupancy on some of their properties with the majority funneling in through their Instagram profile.Another place to look for STRs could be Dahlonega, GA.

Maybe refinance in a few years and buy your first investment using the money you’re going to get out of refinancing?

Well worth the money.

if so, what would be the best way to get the money to fund this without having to do partnerships?

I’m having a bit of paralysis when it comes to actually pulling the trigger on any deals.

I’m currently have all my money in a live in flip but see opportunities all the time.

I am re-reading 'The book on Rental Property Investing' by Brandon Turner then going to re-read 'The Book on Investing In Real Estate with No (and Low) Money down' by Brandon Turner and 'Buy, Rehab, Rent, Refinance, Repeat' by David Greene.