.🚨 Common issues I see:❌ Not properly tracking repairs vs. capital improvements❌ Missing out on cost segregation & depreciation write-offs❌ Scrambling at tax time instead of planning proactivelyI’d love to hear from the group—what’s been your biggest tax headache as an investor?

While you work on that, you could also explore creative financing options like DSCR loans or partnerships to fast-track your first STR.

I don't want to violate any of the self-promotion rules on this thread by specifically linking or name-dropping, but it's from a data analytics platform I am working on specifically built for tracking construction, debt, and ownership activity in the Philadelphia region.I will be posting more detailed insights soon. 

.- Managing Multiple Projects Simultaneously: Handling numerous properties at different renovation stages requires effective project tracking, milestone-based contractor payments, and solid contingency plans to navigate potential delays.- Technology & Automation: Utilizing project management software, such as Buildertrend or Monday.com, enables real-time tracking of budgets, schedules, and contractor communications.

I still need a way to track each tenant’s water usage, so I’m considering the Moen Flo Smart Water Monitor.

Most hard money lenders will want to know about your track record - if you have no experience, partnering with someone who has a track record will likely be an easier path to approval (and likely higher leverage) than applying by yourself. 

Consider connecting with local REI meetups, hospitality groups, or even online forums like this one to find like-minded investors.You could also pitch your successful track record to potential equity partners.

Why ask: You want to know the mentor’s qualifications, expertise, and track record in the specific area you need help with.

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).

A reputable title company will keep things on track.