I have a few concerns that I wanted to get people's thoughts on. 1 - Selling a quadraplex 10-20 years down the road seems like it may be challenging as the market for that type of asset is small.

The fact that some challenge this method is great.

It is challenging in the winter months as people tend to focus on the holidays, shopping, dinners, parties, etc.

One of my rental properties is located in a low-income area, which presents unique challenges in finding suitable tenants.

You’ll often see sales with 100-200% swings within the same area, which makes having deep local knowledge and understanding the nuances absolutely critical.I do this for a living, and even with experience, comping in Detroit can still be challenging.

The challenge is knowing if the listing agent actually tells your offer to the seller or not.For example, if a distressed property is $650k and you want to offer $620k, the listing agent says the lowest the seller may accept is $645k, but is that actually true or made up because the listing agent wants their commission?

- Network with local agents and investors, so you start getting first crack at new deals.If you can amp up the cashflow on the first duplex, you can use the extra cash to:- Pay down the mortgage, setting yourself up for a future refinance to free up your VA Entitlement.OR- For your next acquisition.One of your biggest challenges will to keep the cash flowing when you move out of a duplex.

And you have to challenge their asking price. 

Then use the extra roommate rent income to pay down your mortgage and look to refi to a lower payment in the future (3-5 years) - so it cashflow when you move out.You could also choose the smaller unit and STR the other unit to generate more cash to pay down your mortgage and refi, so it cashflows when you move out.Bottom line: you'll have to get creative to solve your cashflow challenge!

New built for starting out could be a bit challenging.