Hi Kana - I think it depends on your budget of course.

And, depending on where your properties are in Portland, the value might be near its peak—selling while they’re in top condition could be a smart move.Ultimately, it comes down to what will give you the most peace of mind and the most flexibility for the future.

Depending on the types of roles, I may be able to get you some resources.Good luck! 

Quote from @Treza Edwards: I would be looking at this as a market-dependent change.

The amount of capital required from your savings to purchase multiple properties depends on the appreciation rates.

(Usually you cannot use prior employer history until you have been at your new job for 6 to 12 months, depending on the underwriter to show that you are maintaining the same level of bonus/overtime/commission income that you had at your prior employer).

With your budget, depending on where you are working, I'd consider Silver Spring or Hyattsville  

Second, success often depends on creativity, persistence, and a willingness to negotiate.

I ask this because Buildium, also a RealPage company, can actually be more affordable depending on the door count and whether you manage on behalf of others.Buildium, like Appfolio, has different tiers of membership.

The local investors will need to know their local real estate and rental markets and depending on the infrastructure the investor has in place or is willing and able to build, that will dictate how much time and effort they would need to contribute.