tbd Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I’d recommend starting slow with one 2-4 unit using leverage and see if you even like being a landlord.

@Tove Fox hope you find this copy & paste useful:)-------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

For example, I would recommend touching base with local landlords in the market you're wanting to do section 8 investing in to get a feel for how the local section 8 office handles landlord/office relationships. 

Are there tools (i.e RentRedi) that you recommend using for LTR tenant screening, rent collection, background checks, etc?

Talk to your insurance provider about your concerns and they can recommend the right coverage.

Any recommendations?

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I asked a ton of questions of both Fund and Grow and Plastiq, and I highly recommend you do the same because every deal and financial situation can look different. 

We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).