As a starting point: -If they work full time and make $700k a year -Don't want to or can't spend time self managing a short-term rental -Don't have a spouse who wants to take the lead on managing the rentals They are likely not going to directly reduce their taxable income with real estate year-to-year. 

Direct to seller.

I expect conventional to be lower than DSCR.  

Potential Marketing StrategiesShould I directly contact insurance companies to be added to their approved rental property lists?

That'll help you figure out what direction to aim in before speaking with a bank to figure out how much you can qualify for. 

The down payment might be a little higher, but it will be a much longer-term loan that you won't have to worry about coming up with big payment in month 24 and it'll be amortized over a much longer time period (probably 25-30 years), so the monthly payment could actually be lower. 

Quote from @Shawn Questa: A few times I've reached out to Cash Buyers and they would tell me that they are a part of an Investment Group and that they are ready to quickly Close Deals would be happy to work with me.Later I would come to find out that they are actually a Group of Wholesalers, like me.I guess I would prefer to Work directly with the Investor, Cash Buyer or Flipper. 

I live in California (Central Coast) and have built a 12-door portfolio in Detroit, which has been a great market for both cash flow and long-term potential.Detroit still offers properties well below the $150k mark, with strong rent-to-price ratios and a market that’s seeing growth in key areas.

If the seller already has an agent, the agent is his/her legal representative so it's better to deal with the agent directly than the seller.

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