Or you can offer a low enough price to make sense.

Conservative and low risk. 

I’m also open to exploring short-term rentals, private lending, or passive investing in funds—anything that maximizes returns while keeping risk and time commitments manageable.For context, I’d consider leaving my job if this could become a full-time venture that surpasses my current compensation (low-mid six figures).

Once I sell that I’m gonna convert to a fourplex and do the ADU.going through cash quickly and also using credit cards when possible like to purchase materials.

• The “Tour Guide” makes the opposite mistake: they spend all their time pointing out flaws and justifying a low offer.

The lock-in effect of the period from 2016-2022 when interest rates were super low, causing owners with those low rates to not want to sell? 

You may find this a viable option with rates where they are, especially if your rental income continues to cover the mortgage.Home Equity Line of Credit (HELOC): If your property qualifies, you could use a HELOC to access the equity without disturbing the current mortgage.

But the risk to the seller on this deal is immense you have a guy tying up a property who has no ability to close it and then sell it to whoever will give him money and that person could be nefarious get into title rip rents could give 2 craps about the sellers credit etc etc..

We both have good credit but my lender made it seem like there was no getting around putting less than 25% down on an investment property.

Let brokerage grow, tenants pay down mortgage, and save up for another property organically (Cons - slow growth, waisting equity// Pros - low risk)2) Cash out the $300k brokerage account, pay off the townhouse, start cash-flowing $2,400/mo, and save up for new investment or 1031 into multi family(Cons - cap gains tax on cash out, high Oregon income tax penalty, hard to find deals being $2,400 monthly cash flow) // Pros- cash flow, increased leverage into large investment)3) Cash out $300k brokerage and put into separate Multi Fam property, hoping for $2,400/mo+ cash flow, keep townhouse rented as is (Cons - cap gains tax on cash out, not utilizing equity PROs - increase portfolio value, higher upside with value add or rent increase on new units?)