We would GREATLY appreciate feedback from experienced investors on how best to start out on our REI journey.Ok Gabe, let's reverse engineer this a bit to get to a fact-based answer vs opinion or feelings. 

Approaching it logically, an agent is a transaction-based relationship.

This is based on limited no. of States - couple of states including FL mainly.I am very close deciding not to pursue rental property with any HOA and/or CDD.

Was it a market based decision or a quality of life one?

I can share which areas we like to invest in based on price to rent ratios, etc.Elenis

Far too many taxpayers draw up their tax return in their head without a real plan.

When it comes to handyman, I wouldn't necessarily base it on rental property vs. personal.

I know based on the Illinois Condo Act, HOA should cover the wall, insulation and electrical. 

It can be a flat fee with a sliding scale based on sale price.

Yes, based on that, it is possible, especially if it went down from top to a lower floor on a wall side.