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The 401k is a valuable asset but its my thought that I can use this asset to further increase my portfolio by putting that money to better use.

The baseball season lasts 6-7 months, and I am given free housing during this time, wherever I am currently assigned to play.

Before investing here I suggest you read The Ultimate Guide to Grading Cleveland Neighborhoods to get yourself an understanding on the market.

I imagined that to mean that a 1920 home with no renovations would cost more to insure than one updated to 2024 specifications.Is this something that is just "known" to flippers/renovators and I am just coming across it?

This also leads owners to ASSUME simpler is better when it comes to management contracts.

But I’m thinking of getting into STR investment and become more active.I’m a complete newbie to short-term rentals (STRs) and eager to wet my feet in this area.

While this insight is valuable, it’s important to remember that thorough analysis is always crucial before making any final decisions. 

Has anybody invested with them who can provide some valuable feedback?

I don't mean to throw shade at my fellow Illinois residents, but I'm quite bearish on this state for the long-term.