Our initial goal has been to buy a property every time the Army relocates me (roughly every two years) and rent it out afterward.

80% on primary and 75% on investment property I believe.

In the last 18 months various states have instituted new rules, regulations or laws related to (1) need for licensure to wholesale (2) restrictions on marketing of a property in which you do not have ownership and (3) disclosure requirements when dealing with a homeowner that makes it clear to the homeowner that the contact signed with the wholesaler is not a definitive “sales” contract, therefore making it less likely home owners will sign4.

I’m in the process of purchasing a second home in Aspen, CO, which will also serve as my first STR property.

I currently own (and property manages) one investment property (2 family rental).

I took quite a break from buying properties and now on the hunt again.

You are 18, you shouldn't be ready to buy a property yet.

Remember, in this model, you are planning on holding on to these properties as rentals so pay now in quality, or pay later in headaches and repair costs.

However, if the property is sold while financed (there is a loan on it), a portion of the gains will be subject to UBIT. 

Pay particular attention to the "End the complaints" section.HOW TO SHARE UTILITIES 101You have a property with two or more units and the utility meters are shared.