Agents are one thing but you should NOT be having his attorney draft all the docs and not have anyone on your side representing you.

But the biggest cost I can see would be having to get a securities broker involved.

I'd recommend a pet fee at least just in case they're not well behaved.

If total startup costs are over $50k, the deductible amount phases out dollar for dollar.You seem to be having difficultly conceptualizing how one explains to the IRS a non-zero beginning tax capital account on the first return filed or a beginning tax capital account on the return that doesn't match the most recently filed return with an interim period of no filing obligations between the two. 

If a step is missed or done incorrectly, you may find yourself starting all over.How the tenant behaves reacts is anyone's guess. 

@Prasad Reddy  - This is a conversation you need to be having with your accountant

The way that I think and behave will not mesh well with the standard path people take (college -> internship -> decent job -> work until 63 -> retire), I feel like I would be doing myself and the people around me as well as my future family a disservice by going that route.

There are a few like Bayview or Brewers Hill that have gotten better, but for the most part Milwaukee is behaving pretty linear and therefore relativley predictable.

(I should say I think some people behave worse than cattles though).The Dow was at an all time high before the shelter in place. 

For both your buy & sell transactions, it comes down to how buyers & sellers behave when one party is in breach of contract.