I purchased the house for $145,000 and they were asking for $180,000.

National economic trends, local economy, neighborhood situation, home condition, desirability as a rental, demand factors as a purchase, and too many other factors to mention. 

Purchasing the right home every 2 years, then renting it out to someone and purchasing a new home.

I just purchased a SFH that we are rehabbing and will rent for a buy and hold.

Once you've identified your market and where you'll be purchasing to house hack (or if you'll do it out of the home you're in today) you'll be off to the races to start your journey.

HelloI am looking for some help in considering the purchase of a family members property. 

We are additionally looking for a CPA, and we have already received some legal council.We own a single family condo on the north shore of Massachusetts, and just purchased, with the help of my father, a 4 unit apartment building in the same city.

Purchase price: $18,000 Cash invested: $245,000 Sale price: $335,000 New Consruction spec home built with the help of a hard money loan from Upright (Fund that Flip at the time). 1420 sqft, 3 bedroom, 2 bath home on 1.8 acres.

Purchase Price: $39KRehab Cost: $32KARV: $100K  As you can see from the pictures, We redid mostly everything here; Windows, doors, flooring, kitchen, bathrooms and drain tile in the basement. 

I highly recommend that you utilize a low down payment loan (preferrably 5% down since it has less closing costs, you can get out of mortgage insurance once you hit 20%, and you save your FHA for another purchase) and move into a 3-4 unit property.