I am very confused how it could be so high.

The likelihood that you will be able to refi and get some better cashflow is pretty high.

Some background I am retired and sold down some of my highly appreciated rental business assets in early 2024 and I will have around 1/2 Mill Capital gains for 2024 taxes.

At first glance though, it looks like investors can go as high as they want (while still qualifying for a loan) and as many times as they want.

And application cost way too high 297 non refundable.

However, being close to the National Park makes typical travel time longer and being closer to the Four Seasons Resort can be accompanied by high HOA fees.

I like Dayton or Columbus more because they have more going for them across the board, but doubt you can find a quality multi up to your standards at $150K in those areas.

If you're interested in multi-family, I highly recommend starting out with multi-family with your first VA loan as it will be easier to get a single family residence after that.If you decide to pursue multi-family, you'll want to ensure that each unit is separately metered for utilities (water, gas, heat, electricity, etc.) as this is a requirement under VA financing.  

I'm reaching out to see what best practices, behaviors, tools, etc. will help me find the right markets across the country for different investment strategies? 

What I've found is that a simple Zillow skim can help give a rough determination of ARV based on comps in the area (sq ft, #bedrooms, quality of furnishings, etc).