Not as walkable, however, as some of the neighborhoods that you have referenced here.  

Hey @Ana Mills, this ultimately depends on what your current portfolio looks like, your entity structure, and your plans to scale or not.If you have a few STRs and no plans to grow, it's beneficial to have separate bank accounts and credit cards for each property.If you plan to scale to 10+ properties and hold each property within it's own entity, maybe just a checking account per entity and keep some credit cards at the holding company level. 

Because I park it at home and we cant have a business vehicle parked at home .

You want to properly classify transactions such as Contributions/distributions if they are between the entity and the owner itself.If the entities are not direct owners, you have have a Due to / Due From to properly keep track of money owed between the entities.Best of luck!

The only way you can break that log jam right now is severely lowered fed rates, but the level of federal debt is such that they're in a no-win situation because there's going to be little appetite these days for buying 1% fed notes from overseas.The fed rates were kept too low for too long.

(Making judgements based on family status, number of kids, medical animals, etc etc..)4) When you get that first repair call 10pm Saturday night for a leaking roof or water heater do you have a trusted/dependable guy to call and get it fixed that night?

Not sure what suburbs you are referring to, but I have a lot of clients that are very successful investing in areas like McHenry, Woodstock, Elgin, Antioch, Mundelein, Belvedere, etc. 

Do you have a strong lease that you understand and can enforce?

Also for some lenders this has to be cash or if a HELOC is used, they will require the HELOC to be repaid at closing of the delayed finance.

The passive losses will be valuable when you sell a property assuming it’s sold at a gain and you don’t want to do a 1031.