Also, in this market, almost all sellers will require a pre-approval letter, why not get one now even if you're not entirely ready to buy, so you have a better roadmap to your 1st purchase.Contact at least 3 mortgage brokers/bankers who are experienced in your area. 

An alternative thing to consider, if you both have strong incomes, you may want to determine if your borrowing ability (number of mortgages) would be greater if you purchased, and mortgages, properties individually (some in your name, some in your wife's name).Since you are thinking about this all upfront, this would be a good time to sit down with your wife and lay out a roadmap of your near, mid, and long term real estate goals and then meet with an accountant and attorney who specialize in real estate to determine what ownership structure best fits your initial needs and how/when you would move towards more structured (i.e. corporations or trusts) ownership and how to minimize your tax situation in the process.As part of your self-education, I would recommend picking up a copy of Steven Cohen and George Dube's "Legal, Tax and Accounting Strategies for the Canadian Real Estate Investor" It will be a good primer on the subject. 

I plan on keep 2 residences to escape the winters in CT and travel as much as possible.In the other post I touched upon my "Road to Retirement" which is basically a excel roadmap on current holdings, calculating contributions, then using 5% future values to age 55, 62, 67, 70.

A road map to reach qualified, interested, potential investors8.

That agreement had a clear start and a clear finish defined and was used as a roadmap for how the investment would be handled. 3) Since I was partnering with a general contractor, we ran the project through their business to take advantage of the systems they already had in place, and then billed the project for any administrative burden we used at cost. 4) Financially I gave my JV partner's business cash, structured as a loan, that represented my portion of the deal's equity.

No, it's about having a solid game-plan, a road-map, and each thing evolves along the way, right. 

The best thing is the knowledge I gained gave me a road map that made each step of the process very predictable – hence, not stressful!

We need to be extremely wise with what we have because we would like to create a roadmap toward retirement in 15-20 years.

Account ClosedA financial adviser (who's practice is broader than mutual funds and the stock market) would be a good resource in assisting you to draw a road-map of your financial objectives.  

There's much more to it than that, but that's the basic roadmap.