Specifically with mailings, I would talk to your broker, let them know what you are looking to do and see what they suggest, they're the experts on advertising regulations ... and you may have signed something in your independent contractor agreement with the brokerage when it comes to advertising that will apply to no other agents on here except for those within your brokerage.

This would be for both Illinois State Tax and US government filings. 

I do know San Diego is pretty strict against short term rentals so obviously look up what their regulations are.You mentioned a granny flat and splitting the house, so if you're going to be having some sort of shared walls it may be best to put that in your listing as I have seen some people get negative remarks by not mentioning that the house is shared with the owner or some other tenant.As well as lining up two to three excellent cleaning crews, the easiest way to ruin your profit is to start receiving negative reviews for cleanliness and or falsely advertising what your place really is.

You could choose otherwise but you first need to confirm with your landlord tenant regulations as to how 60 days is defined.I would plan on giving her notice near the end of February and the termination date would be the last day of April.It is within her rights to have the court hold her rent however that does not mean the court will rule in her favour on the matter.

Then renewal fees every year can be a burden but again at this point in one's REI career, the cost is outweighed by the opportunity.For a simple breakdown, here are the pros and consPros: MLS access, not reliant on someone else to see the MLS or to literally go view the property, ability to make money off of it, list your own deals..Cons: Fees (annual and upfront), continuing education of laws and regulation (i.e. time not spent on finding deals), always legally disclosing you're licensed, dealing with brokers taking a %Now, these aren't all the pros and cons but certainly some popular ones.

Are there any rules governing the listing specs on rentals?

If you have MLS access cross reference that with reliable real estate data (news articles, studies, government agencies) to find where the hot areas are.I'd say it all comes down to knowing your market and your audience.

I'm wondering how much rehab costs this would entail, and also how much of a hassle it is to deal with zoning regulations.

If you take a heloc against your primary home I understand it's possible to get 90 to 100 ltv. After you get the line of credit are you allowed to move? How long must you stay there? Not trying to get in trouble here....

Otherwise you are selling it contract for deed which while legal is pretty tough to follow the regulations required of you.