@Nicholas LIt appears that you are conflating costs and expensesCost is typically a one time event while expenses occur on a daily basis for line items associated with the operation of the property

One of the principal industry concerns about the vast power granted to the Consumer Financial Protection Bureau was that these powers were too insulated from review….The ruling sends a crystal-clear message to federal agencies that their powers are not unlimited…We would not be at this point today if government agencies were more prudent and consistent about staying within their statutory authorities, grounding their rulemakings in empirical facts, and heeding appropriate procedural safeguards…Instead, too frequently, our regulators appear to be chasing headlines and short-term political wins.”National Association of Homebuilders - “Today’s Supreme Court ruling is an important step forward to advance meaningful regulatory reform because it means that federal agencies can no longer continuously change the law – and the intent of Congress – by implementing their own interpretation of statutes as long as the interpretation is viewed as being ‘reasonable.’

Do they appear well connected online and in real life?

Quote from @Dylan Ritch: Your problem appears to be analysis paralysis.

It appears you are planning to Proceed with caution which would be my advice.  

I personally budget about 200/mo during underwriting and try to maintain a large cash/cash equivalent position.

Obviously paying interest on underutilized capital is sub-optimal but when factoring in the cumulative proposed transactional savings, the annual total interest cost could be equivalent or lower than the net of an alternative home equity line of credit on the same principal loan amount.One 'hack' could be to delay the actual closing of the DSCR loan until a quality purchase prospect is identified and/or near under contract.

Often old houses have some rooms which are not flat even if they appear to be so to the eye.Also, when you are spending money, you want to make the biggest difference for the cost.

Then hover over services, a drop down box will appear and click select short term rentals.

Every system you try will have flaws, or you may salivate over a feature that appears in other software.Some familiar names are mentioned frequently: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I recommend conducting thorough research on each app online to understand their offerings, pricing, etc.