I’m starting a wholesaling company based in Wyoming and interested in operating in Texas and Florida as a start.

Since you're open to markets beyond NYC, you might want to connect with local investor meetups or REI groups in those areas to build relationships with agents, wholesalers, and lenders who understand the nuances of each market.If you're looking to break out of analysis paralysis, maybe start by narrowing down one or two target markets and running numbers on actual deals.

A little background: Feel free to scroll down for the main reason of this post...I started out in 2011 trying everything to make my start in real estate but was not successful until 2015 when we purchased our first duplex in Fresno CA.

House hacking and multi-family properties are great ways to start in real estate!

Rents have gone down since I started my research.

Starting locally vs. out of state:I always recommend starting locally if it aligns with your goals.

Do you think purchasing a property in Philadelphia, PA, and managing it remotely from Westchester, NY (Roughly 2-2.5 hours away) with the help of a local handyman would be too much of a stretch?

There's a reason that people try to buy properties off-market and that is because you can find sellers who care more about terms than maximizing returns.So start with a conversation: you already presumably have some rapport since it's your landlord and you've spoken before.

Here are some financing options to consider:HELOC or Cash-Out Refi on Another Property – If you or your mom have equity elsewhere, this could be a more flexible and lower-interest option.Business Line of Credit – Since the property is in an LLC, you might qualify for a business LOC, which could cover construction costs.Private Money Lender – If you’re okay with 12-15% rates, a private lender could fund this as a short-term loan, especially if the guesthouse will generate strong income.Construction Loan – Some lenders offer short-term construction financing, which converts to a longer-term mortgage once completed.Seller/Partner Financing – Bringing in an investor or structuring a joint venture with someone willing to fund the build in exchange for a share of the income.Credit Card Stacking or Unsecured Business Loans – Riskier but could work if you need to bridge a gap until the unit starts cash flowing.Would love to hear more details—especially your timeline and expected rental income.

Do you also use Redfin/Zillow as a starting point?