When I found the property I simply extended the radius of my search and tadaaaa "duplex" cought my attention and especially for a $350k purchase.

Hi,I have been looking at some of the resources for inspecting properties and estimating costs on this site, and the ones I have seen are detailed spreadsheets and multi-page checklists.

We are working on getting a new insurance policy for one of our properties. small 3 unit property on the Oregon Coast.

You'll want to take a spreadsheet and create a list of all properties you've purchased...particularly in the last 36 months and include the address, lender, purchase date, either rent you receive or disposition date, how much you sold it for, how much you rehabbed it, etc.

Roughly 1,600 sq ft. 2 stories.The alternative is to repair, pressure wash & paint the property costing roughly 4k-6k due to the amount of labor.

After 8 years or so, you've got three or four properties and the world opens up to you at that point. 

I'd say the biggest landmine to watch out for is our property taxes.

If you're looking for ways to accelerate, consider these options:Seller Financing – Some sellers may finance a portion of the purchase price, reducing your need for a large down payment.DSCR Loans – These loans focus on property cash flow rather than personal income, often requiring only 15% down.Private Money Lenders – If you can find a PML willing to work with you, you may be able to put less down.Partnerships – If you’re open to splitting profits, you could bring in a partner who funds the down payment.Since you’re okay with the slower path, just keep stacking cash, but these might be worth exploring to move faster!

I would make improvements to the property only when doing so would cost less than the value added to the property.

As you alluded to, sometimes a passive note investment purchased for monthly payments “goes south”, and becomes an active participation investment, with plenty of additional capital required for legal fees, forced place insurance, and property taxes.