Casual investor in short term rentals

[Shabeen Jafri]

I am already employed full time doing work I love as a software developer and program manager in the DC suburbs..  I am looking to invest in vacation condos in places my wife and I enjoy visiting.  The goal is to get a network of properties to use when we retire and that will eventually provide our children with income.  By renting them out as short term rentals on VRBO, Homeaway, etc.  I hope to offset the purchase cost and (perhaps) make a profit.

I currently have one long term rental in Silver Spring, Maryland.  It was the first house my wife and I bought.  I am likely going to sell it when the current tenants leave to get some capital to buy more short terms.

I am currently looking to purchase in the Orlando area.  Hoping to follow up in other areas we like including the Finger Lakes Region, the San Francisco Bay Area, Niagara Falls, and Hawaii.

I welcome advice and guidance, realizing I am still learning.