Option 2: Electrician recommended mini splits - said 2 units should do the trick and would cost around $6-$7k.Heating system 2 is forced hot air oil furnace specifically for the 3rd unit.

For this reason, I often recommend setting up separate LLCs for Illinois investments.

We do not require you to use our affiliate title companies but we do recommend certain title companies for faster closings. 

Readers should seek professional advice.

It also depends on how you hold your properties; LLC, S Corp etc... as to what the agent will recommend.

Many people choose NOT to have this, because the administrator will then vet every investment you make to ensure you do not invalidate your IRA.Invalidating your IRA means that you've done a prohibited transaction and the entire account is then deemed as distributed to you.If you don't want checkbook control, then I recommend a plan administrator such as Equity Trust - www.trustetc.comIf you are sure that you're aware of all the rules around prohibited transactions and disqualified people (who you can and can't do business with), then a plan administrator like Sense Financial would be a good place to start talking.  

It's obviously not a ton of money but how do you guys recommend me investing with it?

I'm looking for neighborhood recommendations in the Sarasota area for a short/mid-term single family or townhome investment in the 400k-500k range.

I would suggest looking into Hemlane, I have worked with the CEO personally and they have a great product that I recommend to all self managing landlords. 

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?