Advice humbly requested for a RE newbie

[Derek Heinz]

This is my first post, and I hope you'll go easy on me. I'm hitting "create post" with a lot of trepidation. I know how this can go because I am an experienced fly fisherman, and whenever a fishing rookie posts something dumb in a fishing forum, people lambaste them. Please don't do that to me! Remember how it feels to be new at something.... Oh, if there are any Seattleites willing to trade RE intel/mentorship for fly fishing lessons, I'm your guy! 

I am hoping you might give me some good "next-step" advice. I just bought a single-family home (sold a condo rental via 1031) to rent and hired on a property manager since it is 200 miles away. It will cash flow about $200, with tenants moving in next week. 

I own a home that I'd like to rent out, and it would cash flow about $500. If I were to sell it, I'd stand to walk away with about 360k. I do not have much in the way of liquidity, but I do have IRAs and about 30k left in a HELOC. If I go the route of renting out my property, I may just rent a place and wait out the market a bit. My plan -- for now -- is to be a buy-and-hold investor, and I'd like to get into multi-family units. Oh, I'm 49 years old and want to retire from my pretty good 9-5 by 55 and have a nice RE portfolio by then. I live in the Seattle area, if that helps. Oh, and throw in the fact that I'm working towards my RE license and have a friend who wants to partner on a property management company. We have some good mentorship there from a friend who is retiring in another state and turning over his PM company to his kids.

I'm going to assume I'm making the prototypical rookie move and forgetting to include important, relevant info, so please be nice and avoid referring to me as "dumbass" or anything of that sort. Your help is greatly appreciated! BTW, I LOVE BP so far and have been listening to podcasts around the clock, much to my 14 year-old daughter's chagrin.