Does anyone know what my first steps to make sure my taxes are set up optimally?

My goal is to continue purchasing and operating more STRs, and I want to ensure I’m classifying and deducting expenses correctly and optimally from the start.I’d really appreciate any insight or experience anyone has with this situation.Thank you so much,Diana

It kind of does.What ever site you are using needs to be mobile optimized.

There’s a ton of opportunity in those suburbs depending on what you’re optimizing for: Hanover Park and Elk Grove tend to offer stronger cash flow, while places like Morton Grove or Niles lean more toward appreciation and stability.If you’re open to both long-term and mid-term rentals, you’re in a great spot, the northwest suburbs have solid tenant demand from hospitals, corporate relocations, and families looking for good schools.Happy to chat anytime about investment strategy, rent comps, or local submarket data if you want a deeper dive.

While a slight August increase is a seasonally expected trend, last month's sales also benefitted from lending rate optimism and an increase in applications as 30-year fixed mortgage rates eased to mid-6%.

Optimize dynamic pricing — tighten floors 2–3 weeks out; stay aggressive inside 10 days.

You might find the answers to your questions there but I know that the search function is less then optimal so feel free to send me a DM if you don't easily find what you're looking for.I've never bothered commenting much about Canada because, until recently, it made no sense for US investors to invest in Canada: much less favorable mortgage conditions if they could even get one, much more expensive prices on average and much less profitable on average.

Split masters is optimal but not always possible or necessary - but having designated bathrooms for those that are footing the bill can help differentiate your listing.

My focus is on turning distressed or underperforming assets into profitable, well-managed investments through creativity, transparency, and consistent execution.At Real360, we deliver performance-driven property management and investment solutions across Florida, including:💼 Eviction & Lost Rent Coverage🏚️ Malicious Damage Protection🛡️ Liability & Legal Coverage💳 Rent Collection & Maintenance Coordination📊 Portfolio Optimization & Asset Growth StrategiesThis actually isn’t my first time on Bigger Pockets — I had an older account that I lost somewhere along the way.

You might even want a CPA who can handle it all, tax planning, bookkeeping guidance, and strategic advice, so you’re set up for growth and efficiency as your portfolio expands.Here are 3 things I’d look for when interviewing CPAs for a real estate portfolio like yours:Real Estate Expertise: Experience with both long-term and short-term rentals, understanding of deductions, deferrals, and strategies to save on taxes.Proactive Guidance: Someone who actively looks for ways to optimize your portfolio and keeps you ahead of tax law changes.Communication Style: They should explain things clearly, answer your questions, and work in a way that fits your style, virtual meetings, email, calls, etc.Once you narrow it down, you’ll have a much clearer picture of who can help you save the most and grow your portfolio efficiently.