Congrats on going under contract!

 My concern regarding an ongoing issue with my Stessa account.

You’ll want to get really familiar with local zoning laws, short-term rental rules, and landlord-tenant laws as they vary by town if you plan on going the STR route.Focus on Cash Flow Early On: You might be tempted to go for something that appreciates quickly, but in the early stages, it’s important to find properties that bring in cash flow.

REIHub, Stessa, QuickBooks, spreadsheets, etc are all valid tools and depends on the client and how their brain works.I wish you luck in getting yourself organized for the coming season, but would encourage you to make the recordkeeping an ongoing habit rather than a once per year stress fest.

Use a tiered approval process to give them control over larger expenditures while enabling quick resolution of smaller issues.2.Proactive Maintenance: Implement preventative maintenance programs to reduce costly emergency repairs and extend the lifespan of property systems.3.Monthly Reporting: Deliver detailed monthly financial statements that outline expenses, rental income, and ROI performance.By handling their funds with care and providing transparency,  trust is built with owners, ensuring they feel confident in the relationship.Making Tenants Feel HeardHappy tenants are the foundation of long-term occupancy and reduced turnover.

And you can do it with little cash, 5% down conventional is better than 3.5% FHA.House hacking also gives you a chance to cut your teeth in all major skills: analyzing deals, buying process, financing, working with contractors, advertising for rent, background checks, property management.

The appealing aspect here is the ongoing population growth and other economic factors.

I imagine you’re right about the eviction and at the end of the day it will cost me some money, but at least I’ll learn the process and how to better screen tenants (I inherited this one).If you ever get up to Boston let me know.  

There's no strings attached thereafter or need to agree to ongoing PM services.

Unfortunately, my experience has been problematic, to put it mildly:* Communication: There were significant communication issues, including difficulty scheduling calls, which is still an ongoing problem.* Additional Charges: Jenny requested that I deposit on her checking account an additional $20-25k for her to purchase furniture, which I refused because I thought it was very strange, opting to give my card # instead.* Work Quality: Jenny never showed up to the house, she sent 2 people instead, she never mentioned she would not show up herself, she never asked for approval to send two others instead, they did not complete the job, and there were multiple unauthorized charges on my card.* Receipts and Expenses: Once I brought to Jenny's attention that we were 20k above budget, she refused for days to give me the receipts, saying that I needed to give her my credit card statement first.