Cash flow is critical, and I have about $100k ready to go, and possibly another $100k or so from family/friends.

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Note that I plan to keep one unit for my own occasional use when in town, so the conversion isn't critical to my cash flow.

Please let me know if there are critical functions that you have found most useful. 

Proper Budget planning (and understanding) is critical to keep an HOA on the right track.Generally speaking, your Board of Directors is responsible for properly maintaining and operating Associations.

I would stick to an area that has a long history of tourism being a critical component of the economy.

I suppose that it's not critical to cash flow, but I don't want to be losing much money in the short term either. 

rental business is a business's you must look at bottom line numbers.and each market will dictate how much you can pay for capital.in a market like Michealas were she can buy a sub 20k house and rent it for 800 bucks.you can pay HUGE interest rate and still make good moneyIf your paying 400k for a property that brings in 2500 a month then interest rate is a critical component. you need to do the math

I’m a buy & hold investor, and have no experience wholesaling, so take my advice with a grain of salt.What I will say, focusing on learning & education starting out is critical.

Utilize the FHA loan, put little money down, and keep the rest of the capital you have to either invest in the property for strategic reasons and/or have liquid in the bank for your next opportunity, while you live at a discount or for free on the hack.For your expenses, understanding the basics on a rental is a good start(vacancy, maintenance, capex, PM, insurance, taxes, etc), but with it being a small multi-family, knowing your utility situation is going to be critical.