@Michelle SharkoAnswering questions in step by step fashion:- Is it a good thing to do or not is a personal finance decision and it depends on the person asking it, their risk tolerance which in part has to do with how this HELOC or line of credit works and how your personality fares relative to taking on new debt (a person more adverse to debt might have sufficient savings and temperament to pay down/back the debt versus a financially liberal person might get in over their skii's as).

.: Quote from @Chris Seveney: @Dana YobstBlows my mind how he is out there still teaching classes and going on as nothing happened but it sounds like these debts are not getting substantially paid down.As many of us know, one of the main reasons he's able to continue on is with the help of this other self proclaimed criminal https://weclosenotes.com/ep-nc-03-protecting-yourself-using-a-corporate-veil-with-aaron-young-from-laughlin-associates/ Using a remote entity to limit liability is a life blood of insuring investment into all types of job creating, life saving and life improving business development.  

Work with a CPA to optimize your tax returns to reflect sufficient income for future loan approvals.

Same owners, same management (self managed), both STRs.

As a general rule of thumb if the property has a ground level commercial requirement in order to show sufficient hardship to seek a residential use change the property should be located in a location that is not conducive to commercial use i.e residential street, close but not as marketable as properties located on neighborhood's primary commercial corridor etc. 

I would probably only want to buy a condo-tel personally if I were going to self-manage it.

You should either buy with a DSCR up front if the property is eligible and self fund your rehab or hard money for acquisition, do most rehab to common areas with the exception of additional walls prior to refinancing into a long term DSCR loan. 

Quote from @Dongzi Wu: SEC Charges Self-Proclaimed 'Queen of Mobile Homes' and Three Salespeople with Fraud in Mobile Home Investment Scheme This is code for investors money is gone unless there is some bank account somewhere or there are assets.. these deals never end good.

If you only look for the input you want, you won't get the feedback you need.Self-awareness and self-analysis is a crucial part of investing.

I have consulted with a few attorneys over the past couple years regarding this and have determined that for my own personal situation, umbrella insurance provides sufficient risk mitigation for my situation at this time.