Again I cannot collect rent to justify this cost/effort.  

For me, if I make $1500 net per month on a free and clear property I would make $18,000 / year.  

They cost slightly more than the normal permitting process, but I usually have permits in hand in a week or less.My GC is has some experience on Coronado, if you would like I can connect you, so you can get his opinion as well.

Quote from @Sarah Kensinger: I love Minoan and HostGPO also, but Minoan is free to use!

Give your state's 'cure' term ("In New Jersey, a tenant has three business days to pay rent and court costs after a judgment of possession is issued to avoid eviction.

At that class of property, the turn overs are costly. 

Propose starting small, like a single-family rental or house hack, with a clear, low-risk plan to minimize concerns.Leverage your industry connections and offer to handle the initial responsibilities, demonstrating your commitment and capability.

Feel free to reach out and we can discuss.

Not going to give here a lecture on S-corps, but take my word: no benefits, only extra hassle and extra cost, such as preparing another tax return.

Turbotax isn't going to educate you so unless you'd like to educate yourself and potentially make some costly pitfalls, then I'd outsource.