If you’re serious about getting into the game, I’d say build up those local contacts they can be your biggest asset.Glad you’re meeting with someone in real estate financing soon; it’ll be invaluable for guiding you through loan options and what’s realistic for a first purchase.

That’s the hook and to me financing deals seems like the biggest barrier to entry.

The biggest issue I’ve faced is unreliable syncing with financial institutions.

We both have made compromises along the way.I think that’s completely right and one of the reasons you hear the horror stories about these things going sideways (there’s no established timeline for exit), it literally just goes until something breaks. figuring out the ownership structure, and thus the use/access, as well as the exit feels like the two biggest items to get extreme clarity around. 

My 2 biggest issues are getting the occupied units registered as occupied and not Vacant, there is no toggle or selector to do so. 

One of the biggest mistakes an investor can make when deciding to take the plunge and start spending money on Google Ads is targeting the WRONG keywords.It’s true that one way to use keyword targeting is through “broad” keyword types, which are usually less expensive and can capture various keywords you might not have considered in advance.

@Rashim Sharma your biggest challenge will actually be finding a lender.There are two banks that have offices in USA and Detroit that often will lend to Canadians buying in the USA.Can refer you to a Tax Attorney here is the US that has hundreds of Canadian clients with US properties:)

The biggest issue is that eventually those decks will need replacement (I’m keeping them alive as long as I can).

That is one of my biggest motivations and motor to be able to change my invested money for some freedom. 

Having a plan to reduce the price or offer incentives can help get tenants in there faster, which is key to keeping your cash flow steady.Overall, you’re in a good spot with that ADU, and with a bit of flexibility in your strategy, you’ll have options that can really work for you in both the short and long term.