Why ask: You want to know the mentor’s qualifications, expertise, and track record in the specific area you need help with.

They’re often familiar with market-specific expenses and can help validate your estimates.Lastly, as you analyze more deals, keep track of actual expenses on your properties or properties you’ve researched.

If you can brand yourself as someone with a strong track record of getting VA buyers to the closing table efficiently, realtors will take notice and vouch for you and your clients as offers are submitted and this will show tremendous value to borrower clients.  

Which made my tracking for taxes and such all look super dumb because everything is off by a dollar.

Most hard money lenders will want to know about your track record - if you have no experience, partnering with someone who has a track record will likely be an easier path to approval (and likely higher leverage) than applying by yourself. 

Right now the market in Pittsburgh is pretty good for picking up small multi-units.

While you work on that, you could also explore creative financing options like DSCR loans or partnerships to fast-track your first STR.

This will be my first home purchase, and I am aiming to invest in multi-family properties.What should I be aware of when purchasing a multi-family property?

@Charles Perkins is absolutely correct about "collecting all receipts, properly tracking all income and expenses and your basis for all assets properly documented and recorded."

When we moved our companies to a new accounting software we looked at Quickbooks, but found its international awareness (tax rules, multi-currency, locale support, etc), project/job, and multi-company abilities to be clunky.To be fair, none of the candidates hit everything on our wishlist.We ended-up selecting MoneyWorks by Cognito and have been satisfied with it over the past three years.