For the 2-3 months of dry heat, (that most of us spend in the pool or at the lake) we get to enjoy 9-10 months of pure joyous weather without extreme rain, snow, hurricanes, tornados or any other extreme conditions. :)

In cities like Cleveland, Columbus, and Cincinnati, you could buy multiple properties for the same $200K-$250K you’d spend on one in a pricier market.

I have a goal of being able to spend time with my daughter and family.

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

Overall closing out 10 months with Pricelabs I think it is worth it, but I still spend about the same amount of time adjusting rates everyday (10 to 15 minutes for 9 properties).

If you have at least $2,000 to spend or once you scale to that point you could run ads to get your seller leads to come to you and usually these people are just scrolling and your ad pops up that you're looking to "pay cash for homes." 

In 2008 a friend of mine spend $300,000 to buy 100 houses in Detroit.  

On the other hand, a digital nomad looking for a place to WFH for a few weeks will prioritize a private, immersive experience in the location, like cozy lounge seating on a deck to enjoy a mountain or beach view.So while many of the items you mentioned are desirable across the board, it's about tailoring the space to what each group values most based on their needs. 

You definitely wont get an app like that for free, so how much would you be willing to pay to a company to submit it for you, vs spending 10 minutes once a month to submit taxes? 

There are a lot of options out there.Some of the most useful items BiggerPockets members have identified are features that save time so they can spend time working on their next property.