@Avery Oblepias in general, paying for something you can learn online, is really paying for convenience and discipline.It's no different than paying for a personal trainer at a gym.Regarding S8, it's a pretty basic program that $5k seems a bit excessive for.Maybe, $1500?

Not really sure how to go about financing but we're planning on having a down payment at or slightly above $100,000 and don't want to pay more than $3100ish per month. 

Who would be responsible for paying this?

Investing OOS for the first time, and using a TK provider for the first time.I understand I'll be paying (significantly) more for a TK provider home.

To get to the ARV of $250,000 , I am assuming as follow:Because you spent $15,000 in renovation, I am assuming you increased the Initial value of the property at 30,000 bringing it at $230,000Add a 8.69% home appreciation for one year $20,000Estimated Home Value After 1 Year:$250,000Refinancing Breakdown:New Home Value (Post-Appreciation): $250,000 New Mortgage Amount (80% LTV): $200,000 Existing Mortgage Balance after 12 months: -$158,035 Assuming 3 Months Interest Penalty for Breaking Existing Mortgage: - $2371Total Cash Pulled Out: $39,594, allowing you to recover to pay a portion of your initial investment of $63,548, leaving $ $24,015 in the deal.Many new investors mistakenly believe the BRRRR strategy ends after the cash-out.

It may sound nice to pay a 6% management fee but the extra fees can add up to be more than the other company that charges 10% with no additional fees.

You can buy a 250k property with 25% down and pay about $1600 in PITI, or 350k / $2100.

You have to pay people to do things for you, you would normally do yourself.

You can structure the deal to pay him gains at a zero federal tax rate.  

Either he's paying rent or isn't.