Does anyone have any recommendations for a property manager or insurance broker?

The first bit of advice I could recommend is to hire a CPA that knows real estate to ensure you are not missing the easy things.

Also, I grew up in the Rochester area and if you want to be investing in real estate I'd recommend you get out of NY now while you're young. 

I highly recommend listing to @Dave Meyer's most recent on the market podcast! 

There are many ways to get in the game, but I HIGHLY recommend house hacking with roommates if you can.

Deduct NEW property taxes after you buyDeduct home insurance costsDeduct maintenance percentage, typically 10%Deduct vacancy+tenant nonperformance percentage(we recommend 5% for Class A, 10% Class B, 20% Class C, good luck with Class D)Deduct whatever dollar/percentage of cashflow you wantNow, what you have left over is the amount for debt service.Enter it into a mortgage calculator, with current interest rate for an investment property, to determine your maximum mortgage amount.Divide the mortgage amount by either 75% or 80%, depending on the required down payment percentage - this is your tentative price to offer.If the property needs repairs, you'll want to deduct 110%-120% of the estimated repairs from this amount.Be sure to also research the ARV and make sure it's 10-20% higher than your tentative purchase price.As long as the ARV checks out, this is the purchase price to offer.It is probably significantly below the asking price.

I personally don't recommend bothering with an LLC until you have $1 Million in equity.Warning: I am not an attorney, and this can be a complicated topic.

A good real estate accountant can save them thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend that they find a tax accountant who specializes in real estate taxation, business taxation, financial planning and tax planning.I would also recommend that they look for a accountant willing to work with them throughout the year, who can help them strategize and who is responsive when they want to know the consequences of the financial decisions they are making throughout the year.Good luck.

Anyone has a recommendation for affordable yet experience designer to help with few hours of consulting to upgrade the look of   new airbnb?

Investing in Milwaukee for the last 10 years I'm biased to recommend house hacking a duplex as the best way to start if you have limited capital.