The wear/tear is much less for STR because the guests do not live their full-time.   

If you want to buy your first property ASAP, house hacking (duplex, triplex, or renting extra rooms) is one of the best ways to start with a low down payment while learning property management.

I'm a local youth pastor in MN and I'm looking into getting started in real estate so that I can provide extra income for my growing family.

Both of those websites charge the tenants more than $25 and we require all adults living in our units to pay and fill out an application. 

I've been on the western slope for over 30 yrs.I built my primary, its; Slab on grade, stucco, concrete roof, painted with E-84n roof soffits and tailings fire caulk (anti-ember) vulcan fire vents, 4 car wide concrete driveway, extra large house numbers, red 3/4" hoses on reals @every corner, completely denuded of vegetation 100ft.

Quote from @Roxanne Whitaker: Please be aware if you buy an investment property and do not live in MD, when you go to sell it you will pay an 8% tax at settlement. 

I'd highly recommend house hacking in your local market since you're in one of the highest cost of living areas in the US, especially if you're renting currently and planning on staying in the area for 5-10 years.It sounds sexy to go out and invest out of state for your first property.

By adding an extra bedroom, and opening up the 2nd unit by restructuring some of the walls, switching around some of the rooms in the first unit to make it more inviting and give it a larger kitchen.

My main question is should we wait the extra time so we can hold the property longer or should we try and sell this year, take the profit and scale quicker.

Quote from @Sarah Kensinger: Boston is not STR friendly unless you live in the property.