New to REI & new to Portland - Looking for strategy input.

[Travis Jones]

Hello all.  I will be relocating to Portland in April, and would like to start my real estate investment portfolio.  The more research I do, the more questions arise.  I'd like to introduce myself and tap into your knowledge base...sorry for the wall of text.      

About me: Late 30's, respectable salary (125k) in a very secure field, no major capital reserves that I plan on tapping into, FHA 203(k) likely, maximum total mortgage 450k, prefer buy & hold for an extended time, prefer properties in the Portland area (for now), I have a construction background and plan on doing as much contractor work as financially responsible, and I intend to stay in Portland for the foreseeable future.

As far as I can tell, Portland is not the ideal place to make hoards of cash in real estate at the moment.  However, I plan on being here for quite some time and would prefer to be hands-on with my property(ies).  I'd love to create a solid portfolio of cash-flowing rentals that I can hold for 20-30 years.  

Being that a 203(k) is my funding source and I will be required to live in one unit for one year I initially thought to purchase a larger property zoned at least r3 that has an existing structure and is in the low-mid 200's.  Using the rehab loan clean up the existing structure, and utilizing a portion of the foundation, add a modular or steel duplex over a basement thereby achieving 4 units and hopefully all in under 450k.  If zoning allows more units, I would add smaller detached modular / steel units as fast as cash flow allows.  However, I recently found out that 3+ units in Portland are subject to commercial building code which can be much more expensive than residential.

The pros I see are only one property to finance/develop/maintain/manage and the potential for healthy cash-flow.  The con is that it's a massive undertaking, I have zero experience in this field, and I will likely max out my budget on this property and won't be able to buy another until enough equity is built.

The other idea I had was to purchase smaller properties that are sub 100k and build a smaller (1200-1400sf) SFR modular or steel building and an ADU, or build over a basement (if zoning allows MF) and ideally all in at around 150k.  Live in one unit for a year, rent the other, and repeat the whole process every year.

Pros: Very low initial outlay, and a very manageable scale.  Cons: more properties to maintain/manage, land prices will only to continue to go up as eligible properties become more and more scarce and I will have to move once a year.   

The third option would be to buy a preexisting 4 unit, but they don't appear to be priced anywhere near 450k.

Being that I have not arrived in Portland yet and haven't been able to drill down solid numbers in order to put pencil to paper, my projections may be way off. 

I'm not scared to work and I love a challenge.  I like to think outside the box (for better or worse), and look for clever solutions to unique problems.  With that said, I want to develop a solid strategy to ensure my investment is as wise and secure as possible.  

Any guidance you can provide would be greatly appreciated!