The sale price will most likely be around $500,000 and the mortgage is currently about $200,000.I plan on using the profits (let’s just say $300,000) to build an ADU on property that my family owns in Central Oregon.

He's also the least reliable repairman in my market. 

You need an income that meets three requirements:Rents increase faster than inflation to offset constantly rising prices.It must be reliable; it continues even during economic downturns.It must last throughout your lifetime.These are all long-term requirements, so the current interest rates are not the major issue.

If you do not have job or another sufficient source of stable, reliable income, then you'll need a coborrower with good income to be joint on the loan with you to bring the income component to the table.

Building a Team: While I can handle most of the renovation work myself, I’d need an electrician and possibly a real estate agent.

I am still pretty new to the area but I am ready to jump in and start investing in multi-families in the Albany and surrounding areas.  Since this is something that is best done with a team of experts that know a lot ...

Quote from @Kyle Carter: I want to buy an apartment building and rent it out to all section 8 tenants.

What rate, term and amount borrowed did you get for the ADU build and what was the cost?

Section 8 can be a profitable and reliable resource but it is 'their ball, their court' so know the rules first.

Building our PM company has been the most rewarding experience of my career.