There were issues syncing the reservation calendar, and it is nearly impossible to reach a customer support representative with Booking.com as an individual STR owner.

The deal seems to pencil, but the bigger picture stuff makes me nervous. 

It seems like your ROI is basically the same in each option, but you are taking on a much bigger project to convert a single family to a four-family.So basic calculations, since we don't have a full financial picture, i.e. what does financing of each look like?  

Many companies will be lazy/cut costs after they have a large enough customer base.Currently Dataskip.io is the best. 

They just look at pictures. 

As a bulk-delivery service, we have to protect the deliverability of all our customers.

I worked for a big time syndicator in the late 80s and they had 5000 plus investors and customer care was always challenge with no many investors.

Quote from @Daniel Araque: Thank you Georgy, that paints a much clearer picture for me.Essentially it behooves me to pay off my line of credit as fast as possible because the longer it takes, the more interest I'm paying which in turn eats up my total profit for that single investment.I did the math based off the following numbers. $10k line of credit at 8% , 10 year payback, $121/month payment. $1k personal cash flow after all bills/expenses paid.

We enjoy that, but like any business know your customer base. 5.

The question comes with various customized details but it's the same answer over-n-over again, to such a degree that answer-burn becomes a very real thing.