It also had water drainage issues and no landscaping.

Put the pressure on the tenant to pay any advisory or broker fees to their own broker

If they are a high producing broker, they should be able to provide you with an abundance of insights related to that market.

Or maybe rates stay high and he starts feeling the squeeze with his investors if/when he has to refi at 6% or sell at a price I would have paid today.Back to Bjorn's point, keep reviewing and underwriting deals.  

I highly recommend starting by tuning in to the BiggerPockets podcast.

Additionally, the retail sector continues to reel under the pressure of an accelerated shift to online shopping, further exacerbated by the economic repercussions of global challenges.Moreover, the financing landscape has tightened, with rising interest rates putting additional pressure on property owners struggling to meet their financial obligations.

Since interest rate is now high, then IO product becomes interesting.When interest rate is above 6% ; the principal portion of the first 5-8 years is so low that it almost has no point of having principal, so IO loan product becomes (g00d)  product, BUT.....this is the but:1) if i plan to hold the house longer than 10 years hence it's better if I add principal which will reduce cashflow2) but if you plan to house longer than 15 years, and your home appreciate more than 5% yoy, just for the sake of 100 dollar cash flow, then you miss the bigger thing which is appreciation.

However, in general, you should see rents somewhere in the $3k's, possibly as high as $4k if it's in a really good location.

Another clause that I would highly recommend since you are licensed is a buyer's disclosure stating that you are a licensed agent but you are acting as a principal. 

I don't see how building a fourplex would be any different (at a high level), assuming you have an experienced builder lined up to do the construction.