Since you currently operate without an LLC and report rental income on Schedule E, the vehicle purchase might not seamlessly integrate into your existing tax structure.To leverage Section 179 deductions effectively, you may need to consider restructuring your rental property management operations.

Tenant screening, especially here in Chicago, is one of the most important things you have to prioritize learning - learning it the hard way is the fastest, but not always the most cost-effective (I know from experience haha)If you still need a solid eviction attorney, please let me know! 

Their personal problem does not effect your contract in any way.

Knowing what I know now, I will never contribute to Roth; I will only make pre-tax contributions, get maximum tax deductions, invest, and then be selective about which asset I want to convert (such as the one above).  

Surprisingly most zoning in the US didn't come into effect until the 1950's and most lots in developed areas were created before this.  

It also greatly effects the STR and MTR market with the BMT graduations, etc… The last few years have been very slow and the rental market has been flooded with investors at the same time.

I'm always looking for ways to provide value to my tenants while making our rental properties stand out & this seems like an innovative (and cost effective!)

It’s a bit intimidating since it’s outside my usual scope of business, but I’m committed to taking the time to learn how to be an effective landlord.

Can you provide guidance on how to get started and some effective strategies?

@Chris Kay finding a quality, cost-effective contractor is extremely difficult:(There are thousands of contractors that are great talkers, but rarely perform within budget.Standard bait & switch is to lowball a bid, then once they get started all sorts of things "pop up" that somehow their bid didn't cover.