It's the option with the least complications & sets you on the path to FIRE, which is your ultimate goal!

Looks like more complicated circumstance than I expected.

Pricelabs is very complicated.

I'm paying down principle much faster than I would with a 30 year fixed loan and slightly faster than a 15 year fixed loan.It's a bit complicated to explain but you use this loan as your checking account.   

While the bookkeeping will likely be complicated, is the accounting/taxation on this STR based on 100% STR income/expenses allocated 100% to business and general house expenses (mortgage, utilities, depreciation etc) pro rated between STR/personal residence based on sq footage?  

Based on what I remember, it gets even more complicated if the 401k is from a previous employer.In your case, since Fidelity is declining the account due to the nature of the retirement funds, one option might be to consider rolling over a portion of your 401k into a self-directed IRA, which typically offers more flexibility.

You do need to send in a check with the extension, the irs provides guidelines for calculating the amount.Real estate investing complicates taxes sufficiently that I have found I save way more than I spend by having a CPA who specializes in real estate investor tax returns.

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.

I wanted to avoid all that since that (i am assuming) will make things complicated for me not to mention the timely payment of rent.i am in Chicago cook county and in loop..

Furthermore, these bothersome blemishes on the property's municipal searches/reports can complicate future attempts to sell or refinance.A complaint could grab the owner's attention especially if it could lead to a violation, fine, etc.All the best!