Asking about the SW suburbs specifically, in the land of long sidewalks and big actual parking lots. 

Scaling-  your question is both country and even town specific.  

Are there specific lenders or loan types I should look into?

In all the above listed alternative investments, there is seldom any discount pricing and you give up control.

If you want to network or ask specific questions about your local market, go to your local real estate forum and connect with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking5.

One of the most important steps you can take as either a startup landlord or seasoned one is to use a platform specific to property management as it will elevate your operation and save you tons of time.The good news is that nearly every software designed for landlords includes these features.

Alternatively, we can get a 15 year fixed at 5.25% with $8,800 closing costs.

Our buy box specifically focuses on vacation destination accommodations - including boutique motel/hotel, campgrounds, treehouses, cabins, etc.   

If I have several options, I would prefer a HELOC with no initial draw requirements (i.e. to establish a literal line of credit that I have no specific short term plans to use), i.e. not something like the better.com HELOC. 

I’d specifically interested in flipping property.