How will you know for that matter. 

This is confusing.

I too am active duty and have utilized my VA several times to expand my portfolio as it is a great tool to use if you’re willing to live in the property for the required 12 months.

I would determine what the overall look and feel for the STR is going to be and let that dictate what you do.

Request advice from anyone who is either a lawyer in Ohio or is knowledgeable and experienced with Ohio rental laws.

The general reason (avoiding any personal thoughts on wholesaling as a business) is that when you have a license, any fee you get for transacting or assisting in real estate must go through your brokerage and they must take their percentage.

Hard money is not going to take a second position.

Based on your comments, you are at risk of  gravitating towards the lower tier neighborhoods where the spreadsheets will suggest cash flow is better but excel spreadsheets don't tell the whole story. 

You submit a letter of intent to get the property, do inspections first in New York after your offer is accepted, and after inspections are resolved, your attorney then writes the contract.

Purchase price: $55,000 Cash invested: $60,000 Sale price: $245,000 Property is on the market right now.