I would also add that you join your local REIA chapter (Real Estate Investor Association) as it will allow you to network with other STR owners and get more location-specific information. 

Lenders will lend the lower of the amount between LTC and LTV.Do you require an appraisal and survey?

I have experience as a Residential agent in Denver, CO and as a commercial Leasing Associate in Chicago, IL.I am planning to purchase my first rental home here in the next year or so and make it my primary residence.

I am on the board of the RPA (Rental Property Association of Wisconsin, a non-profit) and typically hear if things like this are an issue from our members or attorneys.

For the community development dept, you'll need proper plans (architect), site survey, permits, etc. when you're ready. 

Managing tenants is probably the most frustrating task of all the task associated with owning rental property.  

I asked my local association (PSAR) and was told any list of their MLS only Brokers was confidential.

I don’t have a specific recommendation off the top of my head, but for HOA/condo insurance, it’s usually best to start with a broker who specializes in multifamily or association policies.

If you're lucky enough to get a free and clear property where the seller is willing to finance, this reduces much of the risk associated with seller-finance.I would make sure the title is then moved over to your name, especially since there is not a risk of a due-on-sale clause being triggered.

@Toby FellowsYou are correct, you need to ‘hang’ your license under a broker in order to practice real estate, and most brokerages require you to become a member of the National Association of Realtors as well.While you are preparing and taking your courses, contact several brokers and interview them to find out who might be a good fit.