Then there are the challenges with Section 8 tenants paying utilities and taking care of their rental property.

Challenges?

I’m based in Portland, Oregon, where residential investing seems challenging due to landlord-unfriendly policies and negative cash flow on higher-quality properties.

This does pose a challenge since that real estate is a lot more expensive than if you go more west and south.

Phx has it's own challenges and rewards.

It's going to be challenging to find another house hack with as low of a monthly payment as you currently have, given the low interest rate.

I recommend you call a local agent or broker to give you a better lay of the land so you understand the challenges/opportunities in this area.

By year end I will tackle a MF, value add with my son that would be sweet if we can swing the coop/tic (handling the finance challenges is the hurdle) so he ends up with a unit at below 50% of retail.  

Here are some general guidelines: Lien Position1st Position LienEquityMinimum Down Payment of 20-25% (a 30% equity to sale price is preferred)Down Payment made in certified funds and not borrowedMaximum Funding of 70% ITV (Investment to Value)SeasoningMinimum of two monthly payments already made12 months or more preferredPayer CreditCredit Score of 650 or higherNo major derogatory trade lines (No 90-180+ days delinquent, foreclosure, repossession, bankruptcy, etc.)No decline in credit since purchase of businessTermsPrefer 60 months or lessMaximum of 72 monthsNo Balloon Payment preferredCash FlowBusiness has positive cash flow1.25 debt service coverage ratio preferred.DocumentationPersonal guarantee from a creditworthy individualStandard documents including Note, Security Agreement, and UCC-1 filing.Tax Returns on the business that substantiate profit and loss statements.OtherPayment history current and verifiablePayer Interview indicating buyer is satisfied with business and comfortable making paymentsMotivation for selling the note is not a result of a deteriorating businessConsideration of high risk businesses or geographic areasIn these situations, sometimes a partial is a better option. 

Challenges?