We already have a small portfolio, 3 doors, in Omaha, NE where we live, but the market here has gotten too competitive/overpriced.

Realize most SFH and MFH has been in a Sellers market.  

Learn the basics of financials in RE, build a strong team on the ground, understand the ins and outs of RE and what market your in, understand how to actually flip the home and what strategy you are doing (Highly recommend the BRRR) as holding homes is where the money is made.REAL ESTATE IS NOT EASY!!!

I've always had good luck with Furnished Finder (but in the Denver market).

Every market is different, but here in Pittsburgh the 20+ properties per month that we put out are usually off-market and below market value so a generally low barrier of entry.

To answer your question: As for my market (San Diego) there is such a shortage of housing that even with a steady population we have been near nation high in RE appreciation each of the last few years.  

I have a limited view to the 3-4 markets in which I invest, but I don't see any long term rentals in desirable locations that cash flow year 1.

My main questions would be: how long does the entire process take from applying to actually having possible tenants to start picking from, and how do they determine exact amount for rent (the amounts listed on the housing authority site seem way higher than market rent, I’m wondering if I will actually get those numbers or not)any other general tips or advice is also appreciated!

I started my real estate investing journey this year with the private purchase of a off market house that went awesome.I then found a interesting triplex/warehouse property, went and looked at it with the listing realtor, crunched the numbers and decided that it made financial sense.

@Peter TrifanI would reach out to as many brokers and property management companies in your market for recommendations.