I highly recommend managing them yourself, at least the bill paying, tenant screening, rent collecting aspects, and finding reliable plumbers and heating/cooling people- these are the services you'll use the most. 

The next guests will almost certainly be upset that the hot tub is out of service for their stay and are likely to injure my near perfect streak of 5 star ratings which will injure search rankings and possible lose me bookings.

The older buildings may be in good shape but unless you have full details on the reserves, the board, the upcoming repair work and most importantly the insurance cost and insurability I would stay away from them, especially as investment properties.

If this hypothetical person you desrcibe possesses the operational skills and the investment opportunity is good,  there are plenty of equity placement services out there who will find the needed equity check.

Note that the best tax advantage is expensing the repairs when possible rather than capitalizing and depreciating them.”I bought my property for $400K and it’s worth close to $600K now.

BP is setting up a service next month to connect members and advisors and that should be very beneficial to members looking for professional advice.  

You don't need a co-host, you just need a good cleaning service to handle turnovers. 

In NY it will take 70-90 days to get a mortgage turned around.Fake numbers:* Purchase: $400k* Fees/Transaction Costs/Repairs/Holding: $200kAssuming equity requirements are 25%, you'd need the property to appraise/sell for 800k to get your 600k back out (and return to the lender). 

A no income no doc DSCR (debt service coverage ratio) would be a great option for you .

Indy SFH#1 has a good amount of equity, Indy SFH#2 is currently losing money with all the repairs.