All Forum Posts by: Andrew Street

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Hey There Calvin - That's awesome you're starting so young! House hacking is hands down one of the best ways to get in the game with little capital—live in one unit (or rent out rooms) while your tenants help cover the mortgage. FHA or low-down conventional loans can make it more doable.

Since cash is the biggest hurdle, focus on building credit, increasing income, and saving as much as possible. Side hustles, wholesaling, or even partnering with someone who has money but not the time/knowledge could be great options. Also, network like crazy—go to meetups, connect with investors, and learn from people actually doing it.

If I were 18 again, I’d 100% house hack, stack useful skills (construction, sales, property management), and reinvest every dollar into more real estate. Keep learning and, most importantly, take action. You’re on the right path!

I'd be happy to connect to share more ideas! 

Hey Aaron - Congrats on your first investment property! Opening a separate bank account is a smart move to keep property finances organized. When you set up an LLC, you can align it with the account for better management and legal protection. Consulting a legal or financial advisor can also help you plan this out effectively.

Hey there William - The 14-day personal use requirement applies as long as the loan is classified as a vacation home. Paying down 20% of the principal doesn’t change that—it would still be subject to the original terms. If you want to remove that requirement, you’d need to refinance into a different loan type, like an investment property loan.

Hope that helps!

Hey there Josh - That sounds frustrating! Allowing pets definitely brings in more bookings, but some guests don’t manage them well. Adding a rule that pets can’t be left unattended is a great idea—it helps minimize damage and keeps things cleaner. Some hosts also require pets to be crated if left alone. You might also consider an additional pet deposit or a stricter cleaning fee for excessive mess. Hopefully, this was just a one-off, but setting clear expectations upfront should help!

Hey Pooja - It sounds like you’re handling this situation well by trying to balance your tenants’ concerns with your need to find a new renter. Since your lease allows showings, you have the right to proceed, but keeping things amicable is always best. You might try scheduling as many showings as possible before or after their trip to work around their availability. Another option is to record a video tour before they leave so potential tenants can get a good look without needing to visit in person. If in-person showings are necessary, reassure them that everything will be scheduled in advance and that their belongings will be respected. If they continue to push back, you can gently remind them of the lease terms and try to find a reasonable compromise before taking any further steps. A little flexibility on both sides can go a long way in keeping things smooth.

Hey Todd - Buying an STR in Maui can be a great investment, but there are a few key things to keep in mind. Strict zoning laws mean only certain properties are eligible for short-term rentals, so check local regulations carefully. The market is competitive, with high prices but strong demand for well-located properties, especially oceanfront or resort-zoned areas. Factor in high operating costs like property management, maintenance, and taxes. If you're financing, expect stricter lending requirements. Overall, Maui can be a solid STR market if you do your homework and run the numbers carefully!

Hey Anthony - That's awesome you're getting started! One thing I wish I knew early on is to always run the numbers conservatively—unexpected costs will come up. Also, building a solid local team (agent, lender, contractor) makes a huge difference. Since you're using a VA loan, take full advantage of the zero down, but keep in mind that some properties might not qualify due to condition. If you're thinking about house hacking, it's a great way to cut living costs and start building wealth. Most importantly, focus on long-term appreciation and cash flow, not just getting in fast. Excited for you!

Hey Hailey - I hear you—analysis paralysis is real! If your goal is long-term appreciation and you see yourself moving back to WA, it could be worth the higher upfront investment. But if getting started sooner and building momentum is important, Chattanooga/Nashville might make more sense. A solid local cash-flowing property could help you scale faster, making it easier to buy in WA later. Maybe start where it’s easier, then pivot when you have more capital? Either way, you’re making a smart move—just pick a lane and go for it!

Hey Josh - It really depends on your guests, but a lot of people prefer seeing an all-in price upfront instead of getting hit with extra fees at checkout. Simplified pricing can make your listing more appealing and might help with bookings. That said, if most hosts in your area are still using the standard model, your price could look higher in search results. Might be worth testing to see if it makes a difference! Have you noticed any changes since switching?