I'm currently house hacking my multifamily in Danbury and have another duplex in Brookfield CT that could’ve been a house hack deal as well.My 2 cents are: Stay prepared (preapproved) and on top of the market because when the good opportunities come, you have to jump on it.

One key difference is that Prime also includes monthly bookkeeping in their pricing.For reference, here’s what Taxstra provides for $1,500:• Preparation of individual tax return• Electronic filing of federal & state returns• Review of prior-year return for consistency• Up to two hours of post-filing support for minor corrections/questions• Digital document storage• Short-term rental loophole assistance• Personalized video walkthrough of the tax return• IRS/State correspondence for any notices or inquiries• Year-round access for “quick questions” (not requiring additional research)Does anyone here have experience with either of these services, or have recommendations on what to prioritize at this stage?

That said, staying on top of losses and basis is important and worth the cost of a CPA.

They have a CPA license, 20+ years of experience and their name on the door but they stopped being an expert when they decided what they knew was enough and they were done learning or staying up to date on tax law. 

Hi does anyone have experience with providing direct STR stays (so not through Airbnb or VRBO) and charging, collecting, and remitting the local Chicago hotel tax?

How do you prepare them to receive and manage that wealth so that they don't squander it and/or have it cause more harm than good?

So, Realtors, how/what do you do to prepare for an Appraiser when you feel that the house is at the top end of pricing, yet you got a full price offer?

I assume they use a computer with tax software to prepare your taxes.

I have found someone that has great income and can really afford to stay in the home. 

So make sure he’s got enough coming in to cover that.)Don’t forget your property taxes will probably go up, and he should have renter’s insurance.More difficult if you have siblings to make sure everything “stays fair.”