And I don't think it's a stretch to imagine this happening.

Over $250k is going to be a stretch for where I'm at currently

Since I don't have all that information it's really not a good idea for you to take any answer I might give you because it might be right for me but wrong for you..1031 is usually not an option in syndication because it's designed for "like kind" exchange and while many people stretch the definition of "like" IRS will not take exchanging real estate with securities (in syndications you buy shares of the LLC).Only way to do that is if the sponsors somehow structure the holding in a way that the investors are TICs but I personally haven't seen one done this way. 

She is also has stretched out paying her late fees.

But it's really a stretch of the imagination for new investors (less than 10 years in the business with a track record) to think such loans are an everyday reality for them.

As far as flipping strategies buy right and then also price correctly when you sell.As a real estate broker new product doesn't come on the market every 30 days it comes on the market every week and sometimes daily.Knowing that what buyers want is the best product at the most reasonable price.They don't want a crap hole to live in just because it is cheap.So when rehabbing if your budget is stretched pick 2 or 3 things that will pop and catch the buyers eye that say QUALITY.Also in this market a price drop every 30 days won't cut it.As a broker we know from statistical data that 85 percent of activity occurs in the first 10-14 days on the market.If recent sold prices range from 40k to 50k I want to be in the bottom 50% of list price 40k to 44k with a great product.If I have given it maximum exposure and nothing comes in drop the price every 7 days until it sells.You want to always stay ahead of the pricing curve and chasing the market down.It is the number one mistake made by all sellers.

"Stretching" and seeking new challenges is great and commendable, but make sure you don't make a decision based largely on the apparent monetary gain.

I think they would have agreed with the libertarian viewpoint on individual rights and highly limited government but to apply the social liberal views of today to them is very much a stretch, especially when you consider what John Adams described as a "utopia" - a country where the law of the land is the Bible.

This first property should sell for around 90K including the immediate maintenance it will require.So, we are looking at 20K each carried as home equity loans against our homes, 50K as a commercial real estate mortgage.Should we stretch out the terms for max cash flow now which will allow us to acquire other properties more quickly or should we go with shorter terms which will have slightly lower rates and quicker equity build up?

To begin with, I do my best not to stretch their budget beyond a reasonable comfort level.