The idea of owning and managing vacation homes that provide memorable stays for travelers excites me.

So, $5k/$20k = 25% return on your investment.This is a very simple example that ignores the rental income vs any mortgage payment (taxes & insurance, etc. would be the same in both examples).To increase cashflow, you would also want to take the lower payment of a 30-year mortgage vs 15-year.Regarding the purchase:1) Require the seller to have tenants sign a MTM lease or vacate before closing.

There are programs that offer 100% financing for many different people like Veterans, First time home buyers, (Certain states), Medical professional loans also offer 100% (Anyone with a Medical license).You also have Second Home or Vacation home which only requires 10% down.

And most of the damages a guest will do can be covered by these str booking sites insurance.Your budget will prevent you from buying homes in some of these big cities or vacatation areas with tons of str's. 

High-speed internet, a desk, good coffee etc will be different than a family staying for a vacation. 

People who are able to work their business or job remotely will choose a vacation style locale to live like Florida where we have great weather, no state taxes, and a very low tax rate compared to other states.

Also what type of lifestyle are you trying to maintain-a simple one or one where you go on exotic vacations every month?

The good thing about househacking a legal multifamily unit is that lender allows you to use the vacated units of 75% market rent as an income to offset the potential current mortgage.

I'm seeing 25-30% for STR management in Colorado (more if your vacation rental is near ski areas like Breckenridge or Vail). 

At that point, if your tenant is not willing to renew,  you simply advise the tenant that you will not be renewing their lease, and provide them a move-out date by which they must vacate the property.