Additionally, I mentioned that I had sent them a small holiday gift card as a token of appreciation (which I send to all of my tenants) and wished their family a peaceful and warm holiday season.Your insights helped me craft a response that balanced kindness with maintaining boundaries, and I truly appreciate it.

Seller financing can be a fantastic way to get into a 4+ unit property, especially in a competitive market like Chicago.Have you started reaching out to owners directly or networking with agents who specialize in multifamily properties?

You should have a good idea of every expense you have in your primary home, then add the STR specific:  (These are rough estimate numbers, depending on various factors)STR insurance - a special insurance that covers both the property and your liability, could be $2~4k in areas without natural disasters, could be more than $10k in some other areas.cleaning fee - approx. $50 per bedroom, so a 4-bedroom house will cost you about $150~200consumables - bathroom supplies, kitchen supplies, beverage supplies: $20~30 per week, depending on how much you providewear and tear - towels, linen, kitchen utensils, some furniture: $1000~2000 per yearRepairs/replacement for things that guests break or steal:  $1000~2000 per yearAlso, if your personal use is less than 14 days a year, the entire property's expense is deductible against STR income, but if you use more than 14 days, then you will have to calculate the proportion of how many days it's rented out vs how many days you or your family uses. 

- We recommend 5% after 30 days (or sooner).7) What MoveIn Specials has your PMC discussed with you?

We specialize in short-term rental investments through our integrated real estate, mortgage, and property management services, delivering expertise at every stage of the process.

I’ve personally found that specialized property perks can create stable, long-term renters.

I am expanding to more specialized Airbnb this year.

Bigger Pockets is a great place to find a real estate tax accountant.A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.

I think what it comes down to is smaller with market specialization translates into a better experience

I specialize In helping investors like yourself locate, and secure investment properties and provide a hands off experience along the way.