Immerse yourself around likeminded people and start developing relationships with those in the real estate industry.

It's my opinion based on working in the title insurance industry for several years. 

✓Second Home Requirements must be occupied by the borrower for some portion of the year is restricted to one-unit dwellings must be suitable for year-round occupancy the borrower must have exclusive control over the property must not be rental property or a timeshare arrangement1 cannot be subject to any agreements that give a management firm control over the occupancy of the property must be underwritten in DU and receive an Approve/Eligible recommendation, with the exception of high LTV refinance loans required to be underwritten in accordance with the Alternative Qualification Path (see B5-7-03, High LTV Refinance Alternative Qualification Path).

Incur the expense of refurb and have a forever cost of maintaining the pool is a big deterrent as it adds absolutely zero dollars to what I can charge for rent and there is always that legal liability of an accidental drowning or some accident where the liability insurance may not cover or claim exclusion. 

Is the way that this guy is looking at my finances an industry standard?

@Patrick M. yea I agree, the firm I went with exclusively handles these appeals and stated they have relationships with the involved parties.

The area is not high crime - it is a rural blue collar town that has a good industrial park for people to work.  

I market almost exclusively on FB marketplace and have had great results.

One of the most valuable and important things you can do is to understand the industry vernacular and how it is applied to a real estate asset.Feel free to DM me and will send a few pro forma snap shots.

Looking for people to connect with in my area to learn more about the industry!