I agree with @Mario Dattilo and Roger D Jones.I think the only thing that I would draw emphasis on is what Mario said because unless it has a separate tax ID number it is not an apples-to-apples comparable.

I watched as cheap cash cars were bought with income tax every few years when they got too expensive to maintain.

I am looking to start investing into Tax Lien Certificates/Deeds, but I don't know which way to go. 

I get where your coming from but the point of an LLC is that it keeps the asset protected from all others so in a sense the holding company is just a formality for tax purposes since an s-corp would be attached.If you do a separate llc for each property without a holding company then you would have to make a separate s corp for each property which wouldn't make sense as that defeats the purpose of the s-corp thus the reason for the holding company.

Accounting for the utilities, taxes, closing costs, etc...

If they purchase a house in your area, you could have the judgment attached to the property (I have done this before).Lastly, I have heard that you can 1099 them so they could be forced to pay taxes on it.

DSCR loans look at you liquidity position, credit score, and the rent vs principal, interest, taxes, and insurance.

@Sean McDonnell, one thing to consider is their revenue numbers count all revenue (nightly rate, fees, taxes) so you should deduct those from the AirDNA revenue projections.This is easier to do on a property-specific level since you can roughly estimate the cleaning cost for a specific property.

There are also tax considerations, such as depreciation and IRS Section 121 Exclusion.I would probably keep it as a rental for two years and then consider IRS Section 121 Exclusion; I would probably still keep it as a rental at that point, and if interest rates get below 6% I would consider a cash out refi to buy another investment property.If you do keep it as a rental I would recommend you pay for pool service, this is something that should not be passed on to the tenant as it can cost you big time if not properly maintained.

Baltimore property taxes are also pretty high, quick flips are profitable and if you or your investors know what you/they are doing, Baltimore is a great market.