RentRedi had no ability to manage this.  100 was the primary address of the property, which would show on google maps and such, and then 101 was an additional address that I legally owned and wanted to use (same structure).

This can put a significant strain on your finances and cash flowThey also often require a large down payment themselves and may have a strict repayment schedule that can be difficult to meet, especially if there are unforeseen circumstances or delays in renting the property or generating income from itIn addition, relying on this type of loan may expose you to higher financial stress and the possibility of default if you are unable to meet your loan obligationsThe final decision depends on your overall financial situation, risk tolerance, and your ability to manage the associated costs and obligations

I think the before vs after pictures really speak primarily to your experience and ability to execute a project so it can help lenders gain comfort with future projects and allow you demonstrate what level of detail you except out of your contractors.

I've heard too many stories of investors purchasing homes for STR use, only to find that they lose their permit or the ability to transfer it when they sell.

Your strategy takes advantage of your employment cash flow and ability to control discretionary spending.  

depends on your credit if you can get a mortgage or your ability to find good deals that you use hard money for and then refinance into DSRC.  

Cashflow and the ability to use the property.

With Baselane I have the ability to do everything from initial vetting of the tenant to drawing up the lease to collecting rent (and issuing deposit refunds!)

DSCR (Debt Service Coverage Ratio) loans generally focus on the property's ability to generate enough rental income to cover the debt payment.

Do you want your son to bet the financial outcome of his 20s on this seller's ability to make good choices?