I go with the highest deductible possible.

.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

The primary thing you're going to run into is whether or not a lender, at purchase of the property, will allow there to be a secondary lien on the property.

If Oak Park allows STRs, leveraging that history could make the property stand out.That said, unless the home has been preserved as a landmark or has unique historical features, the value boost may be more about novelty than a significant price increase.

A second mortgage or HELOC might allow you to unlock some funds without losing the 3.25% rate.- I recommend avoiding condos. 

There are a couple of things I like about them but one of my favorite things is that it allow me to control if I will allow partial payments or not.

I don't know a single broker who would allow an agent to wholesale while hanging their license at their firm. 

As with all regions, the Oregon Coasts' counties and cities are tightening their rules (and quantities of allowable vacation rentals) and there are a few adjustments to last year's regulatory landscape.

The flippers who COULD handle the volume that a flipping fund would allow them to take on, don't need a fund, because often times, anyone flipping at that volume is already making close to 7 figures a year, and wouldn't want to keep splitting it.Alternatively, I, personally, would not invest with a flipper that hasn't done it, a lot.   

I do not understand your remark as related to the DSCR loan.  2 ADUs are not allowed by f/f conventional financing but is not always enforced.Fortunately if you stay with the current tenant without a refi, by the time you pay principle it is likely the rent will have increased enough to absorb the increase mortgage payment.