Can I do a 1031 exchange in such a way that the funds in escrow are used to purchase multiple properties?
No. But you can use multiple properties to purchase one. Its exactly like monopoly.
I didn't really even consider taxes when I started doing this. Bought it for $23k, put in about another $30k, and probably selling for around $140k. How boned will I be if I don't do 1031? Also, can a 1031 be used to sell a single family home and buy a multi family or apartment? Assuming the original house was always an investment property.